Related Products 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.
Hexadecanedioic acid (4.5 g, 15.71 mmol) was suspended in Toluene (28.1 ml) and the mixture was heated to reflux. 1,1 -di-tert-butoxy-N,Ndimethylmethanamine (10.10 ml, 42.1 mmol) was added drop-wise over 30 mm. Themixture was reflux overnight. The solvent was removed in vacuo at 50C and the crude material was suspended in CH2C12/EtOAc (75 mL. 1:1) ans stirred for 15 mm. The solids were removed by filtration and washed with CH2C12 (25 mL). The filtration was evaporated in vacuo. The resulting material was suspended in CH2C12 (6 mL), cooled with ice for 10 mins, and filtered. The solvent was removed invacuo to leave crude product which was purified by flash chromatography (silic gel,EtOAc/Hexane) to get 16-(tert-butoxy)-16-oxohexadecanoic acid (2.56 g, 7.47 mmol,47.6 % yield). Analysis condition D: Retention time = 5.04 mm; ESI-MS(+) m/z269.3 [M – OC(CH3)3]; ?H NMR (500MHz, METHANOL-d4) oe 2.33 – 2.18 (m, 4H),1.66 – 1.54 (m, 4H), 1.50 – 1.43 (m, 9H), 1.40 – 1.25 (m, 20H).
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; BRISTOL-MYERS SQUIBB COMPANY; GILLMAN, Kevin W.; GOODRICH, Jason; BOY, Kenneth M.; ZHANG, Yunhui; MAPELLI, Claudio; POSS, Michael A.; SUN, Li-Qiang; ZHAO, Qian; MULL, Eric; GILLIS, Eric P.; SCOLA, Paul Michael; LANGLEY, David, R.; (683 pag.)WO2016/77518; (2016); A1;,
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