Category: 36805-97-7

These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C11H25NO2

Hexadecandioic acid (40.0 g, 140 mmol) was suspended in toluene (250 ml) and the mixture was heated toreflux. N,N-Dimethylformamide di-tert-butyl acetal (76.3 g, 375 mmol) was added drop-wise over 4 hours. The mixturewas refluxed overnight. The solvent was removed in vacuo at 50 C, and the crude material was suspended in dichloromethane/ethyl acetate (500 ml, 1:1) and stirred for 15 mins. The solids were collected by filtration and triturated withdichloromethane (200 ml). The filtrated were evaporated in vacuo to give crude mono-tert-butyl hexadecandioate, 30grams. This material was suspended in dichloromethane (50 ml), cooled with ice for 10 mins, and filtered. The solventwas removed in vacuo to leave 25 gram crude mono-tert-butyl hexadecandioate, which was recrystallized from heptane(200 ml) to give mono-tert-butyl hexadecandioate, 15.9 g (33 %). Alternatively to recrystallization, the mono-ester canbe purified by silica chromatography with ethyl acetate/heptane. 1H-NMR (CDCl3) delta: 2.35 (t, 2H), 2.20 (t, 2H), 1.65-1.55(m, 4H), 1.44 (s, 9H), 1.34-1.20 (m, 20 H).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novo Nordisk A/S; HOEG-JENSEN, Thomas; JAKOBSEN, Palle; SENSFUSS, Ulrich; FLEDELIUS, Christian; RIBEL-MADSEN, Ulla; (32 pag.)EP2448962; (2016); B1;,
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Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 36805-97-7, Product Details of 36805-97-7

A solution of (S)-(+)-Z-4-amino-2-hydroxybutyric acid (5) (5 g, 19.74 mmol) in toluene (38 mL) containing N,N-dimethylformamide di-tert-butyl acetal (18.92 mL, 78.96 mmol) was heated to 95C for 3 h. The solvent was then evaporated and the crude product was purified by flash chromatography on silica gel (n-hexane/EtOAc = 7:4) to give (6) (3.4 g, 55.7 % yields) as yellow solid. Mp 42-44C; [alpha]20D= – 5.9 (c= 10.1 mg/ml, CHCl3) 1H-NMR (CDCl3) delta: 1.47 (s, 9H); 1.76-1.85 (m, 1H); 1.94-2.09 (m, 1H); 2.74 (br s, 1H); 3.36 (dd, J= 6.04 Hz, J= 11.99 Hz, 2H); 4.10 (dd, J= 4.02 Hz, J= 8.05 Hz, 1H); 5.09 (s, 2H); 5.21 (br s, 1H); 7.31-7.37 (m, 5H) Anal. Calcd. for C16H23NO5: C, 62.12; H, 7.49; N, 4.53. Found: C, 62.22; H, 7.48; N, 4.53.

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Reference:
Patent; Bracco Imaging S.p.A; EP2149568; (2010); A1;,
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These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

(b) tert-Butyl1-(trifluoroacetyl)azetidine-3-carboxylate 1,1-di-tert-butoxy-N,N-dimethylmethanamine (16.5 g, 81 mmol) was added to a solution of 1-(trifluoroacetyl)azetidine-3-carboxylic acid (5 g, 25 mmol) and the mixture was heated to reflux for 8 hours. LC-MS showed remaining starting material and therefore an additional amount of 1,1-di-tert-butoxy-N,N-dimethylmethanamine (21.2 g, 81 mmol) was added and the heating was continued over night. LC-MS showed still some remaining starting material (starting material/product about 1/2) and the THF was exchanged for toluene (100 mL) and the mixture heated to 100 C. (oil bath temperature) for 2 hours. The solvent was evaporated and the residue dissolved in EtOAc (200 mL). The organic phase was washed with NaHCO3(sat) (2*50 mL), water (2*50 mL), Brine (50 mL), dried (Na2SO4), filtered and evaporated to give the desired product. Yield: 4.5 g (70%).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US2008/171732; (2008); A1;,
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Reference of 36805-97-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 36805-97-7 name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 10 2′-(6-Carbamimidoyl-1-methyl-1H-indol-3-ylmethyl)-4-methoxy-5′-methylcarbamoyl-biphenyl-2-carboxylic acid; Part A. 3-bromo-4-formyl-benzoic acid tert-butyl ester:; A solution of 3-bromo-4-methylbenzoic acid (5 g, 0.023 mol) in 40 mL toluene was heated to 80 C. in an oil bath and DMF-di-t-butylacetal (22.4 ml, 0.093 mol) was added dropwise over 20 min. The resulting mixture was heated for an additional 1 h and then cooled to rt and evaporated to dryness. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the t-butyl ester (5.1 g, 81%) which was dissolved in 50 mL CCl4 and treated with N-bromosuccinimide (6.7 g, 0.037 mol) and benzoylperoxide (0.22 g, 0.94 mmol). The mixture was then heated in an 80 C. oil bath overnight. Solvent was removed by evaporation, and residue was taken up in EtOAc and washed with water, sat’d Na2CO3 and brine then dried over anh. Na2SO4, filtered and concentrated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the dibromide (7.5 g, 94%) to which was added 30 mL morpholine and the mixture was heated overnight at 60 C. After cooling to rt, the mixture was diluted with EtOAc and washed with 5% citric acid solution until aqueous phase stays at pH 4, then with sat’d bicarbonate solution and brine. Organic phase was dried and concentrated to provide the aldehyde in 74% yield after flash chromatography. 1NMR (500 MHz, CDCl3) delta 10.40 (s, 1H); 8.24 (s, 1H); 7.95 (m, 1H); 7.93 (m, 1H); 1.61 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
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Synthetic Route of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-Hydroxy phenyl acetic acid-t-butyl ester (Reagent E) A stirred suspension of 4-hydroxy-phenyl acetic acid (0.152 g, 1 mmol) in anhydrous toluene (5 mL) was heated at 80 C. and N,N-dimethyl formamide-di-t-butyl acetal (1 mL, 4.17 mmol) was added when the solution became homogenous. After 0.5 h, the reaction mixture was cooled to ambient temperature and the volatiles were distilled off in vacuo. The residue was diluted with water and extracted with diethyl ether (*2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 16% ethyl acetate in hexane as the eluent to afford the title compound as a solid (0.11 g, 56%). 1H-NMR (300 MHz, CDCl3): delta1.44(s, 9H), 3.45(s, 2H), 6.55(s, 1H), 6.69(d, J=8.8 Hz, 2H), 7.06(d, J=8.5 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; Allergan Sales, Inc.; US6313107; (2001); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 36805-97-7, HPLC of Formula: C11H25NO2

To a hot (800C) solution of 4-bromo-3-methyl benzoic acid (3.00 g, 13.95 mmol) in toluene (250 ml_), N,N-dimethylformamide di-terf-butyl acetal (11.35 g, 50.2 mmol) was added. The mixture was stirred at 800C for 8 h and at rt for 16 h before another portion of lambda/,lambda/-dimethylformamide di-terf-butyl acetal (5.67 g, 25.1 mmol) was added. Stirring was continued at 80C for 16 h. The mixture was cooled to rt, diluted with EA and washed with sat. aq. NaHCO3-solution followed by water. The org. layer was separated, dried over Na2SO4, filtered, evaporated and dried under high vacuum at 400C to give terf-butyl 4-bromo-3-methyl benzoate as a pale yellow oil (2.31 g). LC-MS: tR = 1.10 min; [M+1]+ = not detectable; 1H NMR (CDCI3): £ 1.61 (s, 9H), 2.46 (s, 3H), 7.59 (d, J = 8.3 Hz, 1 H), 7.66 (d, J = 8.3 Hz, 1 H), 7.86 (s, 1 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/109904; (2009); A1;,
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Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 36805-97-7 as follows. Quality Control of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

Step C: (2Z)-1-[2-(3-Bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-fluoro-2-propen-1-one; To a solution of 1-[2-(3-bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-2-fluoroethanone (10 mg, 0.025 mmol) in DMF (2 mL) was added DMF di-tert-butyl acetal (0.85 g, 4.2 mmol) and the reaction was heated at 80 C. for 15 min. The crude reaction mixture was adsorbed to silica gel and purified by LC (5-50% EtOAc in hexanes) to give the title compound (10 mg, 88%). ESIMS (M+H)+=456.

According to the analysis of related databases, 36805-97-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US2008/51395; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 36805-97-7, These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 1-pyrazol [1,5-b] [PYRIDAZIN-3-YLETHANONE] (8.5 g, 52.7 [MMOL)] in DMF (100 mL) was added [DIMETHYLFORMAMIDE] di-tert-butylacetal (16.1 g, 79.2 [MMOL).] The reaction was heated at an oil bath temperature of 100 [C] for about 4 hours. The solvent was removed in vacuo. The residue was triturated with diethyl ether to give the title compound as a brown solid (8 g, 70%). 1H-NMR (300 MHz, [D6-DMSO) 6] 8.76 (dd, 1H, J = 10.0, 2. [0 HZ),] 8.74 (s, [1H),] 8.61 (dd, [1 H, J = 4.] 0,2. [0 HZ),] 7.74 (d, 1H, J = 12 Hz), 7.44 (dd, [1H,] J = 10.0, 4.0 Hz), 5.87 (d, [1H,] J = 12 Hz), 3.18 (bs, 3H), 2.97 (bs, 3H); MS [(ESI)] (M+H) [+] 217.

The synthetic route of 36805-97-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/35588; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 36805-97-7, A common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of compound 36 (5.67 mmol) in anhydrous toluene (13 mL) at 110 0C was added Lambdaf,Lambda/-dimethylformamide di- tert-butylacetal (22.7 mmol) dropwise. The reaction mixture was refluxed for 1.5 hrs. The mixture was cooled down to room temperature, and washed sequentially with H2O (30 mL), sat NaHCO3 (30 ml), and brine (30 ml). Organics were dried and concentrated under reduced pressure to yield compound 37 as a yellow oil in 82% yield.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; IDENIX PHARMACEUTICALS, INC.; PARSY, Christophe Claude; ALEXANDRE, Francois-Rene; LEROY, Frederic; CONVARD, Thierry; SURLERAUX, Dominique; WO2011/17389; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine

Preparation of compound (6); A solution of (S)-(+)-Z-4- amino-2-hydroxybutyric acid (5) (5 g, 19.74 mmol) in toluene (38 mL) containing N,N-dimethylformamide di-tert-butyl acetal (18.92 mL, 78.96 mmol) was heated to 95C for 3 h. The solvent was then evaporated and the crude product was purified by flash chromatography on silica gel (n-hexane/EtOAc = 7:4) to give (6) (3.4 g, 55.7 % yields) as yellow solid. Mp 42-44C; [alpha]20D= – 5.9 (c= 10.1 mg/ml, CHC13) 1H-NMR (CDCl3) delta: 1.47 (s, 9H); 1.76-1.85 (m, 1H); 1.94-2.09 (m, 1H); 2.74 (br s, 1H); 3.36 (dd, J= 6.04 Hz, J= 11.99 Hz, 2H); 4.10 (dd, J= 4.02 Hz, J= 8.05 Hz, 1H); 5.09 (s, 2H); 5.21 (br s, 1H); 7.31-7.37 (m, 5H) Anal. Calcd. for C16H23NO5: C, 62.12; H, 7.49; N, 4.53. Found: C, 62.22; H, 7.48; N, 4.53.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 36805-97-7.

Reference:
Patent; Bracco S.P.A.; EP1972617; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem