Electric Literature of 6298-96-0, These common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, 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.
A suspension of tert-butyl 4-(2-(6-methoxypyridin-3-yl)-2-oxoethyl)piperidine-1 -carboxylate (3.00 g, 8.97 mmol) and (S)-1 -(4-methoxyphenyl)ethan-1 -amine (2.00 mL, 13.5 mmol) in titanium(IV) isopropoxide (7.89 mL, 26.9 mmol) was stirred at 90 C. The reaction progress was monitored by LCMS (aliquots treated with MeOH, NaBH4, followed by 1 N HCI). LCMS indicated complete reaction after 1 hour. The yellow solution was cooled to 0 C, diluted with MeOH (15 mL), treated slowly with NaBH4 (0.509 g, 13.46 mmol) in portions. After 1 hour, the solution was warmed to RT and stirred for an additional 4 hours.. The reaction was quenched with saturated aqueous NH4CI and 1 N HCI and then extracted with EtOAc. The EtOAc solution was washed with saturated aqueous NaHC03, brine, dried over Na2S04, filtered, and concentrated. 1H-NMR analysis of the crude material showed an approximately 2:1 mixture of SS : RS diastereomers. Purification by flash chromatography (silica gel, 0-100% EtOAc/hexanes, gradient elution) afforded tert- butyl 4-((S)-2-(((S)-1 -(4-methoxyphenyl)ethyl)amino)-2-(6-methoxypyridin-3- yl)ethyl)piperidine-1 -carboxylate (2.39 g, 57% yield) as clear oil. LCMS (ESI) m/z calcd for C27H39N3O4: 469.3. Found: 470.4 (M+1)+. NMR (400MHz, CDCI3) delta 7.85 (s, 1H), 7.48 (d, J = 8.6 Hz, 1H), 7.12 (d, J = 8.2 Hz, 2H), 6.87 (d, J = 8.2 Hz, 2H), 6.76 (d, J = 8.6 Hz, 1H), 4.08 – 3.88 (m, 5H), 3.82 (s, 3H), 3.40 (q, J = 6.4 Hz, 1H), 3.33 (t, J = 6.6 Hz, 1H), 2.67 – 2.43 (m, 2H), 1.66 – 1.48 (m, 2H), 1.47 – 1.16 (m, 15H), 1.09 – 0.82 (m, 2H).
Statistics shows that 1-(4-Methoxyphenyl)ethylamine is playing an increasingly important role. we look forward to future research findings about 6298-96-0.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EVINDAR, Ghotas; KAZMIERSKI, Wieslaw Mieczyslaw; MILLER, John Franklin; SAMANO, Vicente; SUWANDI, Lita; TEMELKOFF, David; WASHIO, Yoshiaki; XIA, Bing; (152 pag.)WO2019/3142; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem