Analyzing the synthesis route of 123855-51-6

The synthetic route of 123855-51-6 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.123855-51-6,tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate,as a common compound, the synthetic route is as follows.

Di-tert-buty dicarbonate (88.63 g) in toluene (296 ml) was added to a stirred solution of ethyl isonipecotate (62.88 g) in toluene (317 ml). The reaction mixture was then distilled at atmospheric pressure, removing about 130 ml of distillate, with a final distillation temperature of 112C Sodium bis(2-methoxyethoxy)aluminium hydride (Red- Al, 65% w/w solution in toluene, 161 g) in toluene (220 ml) was then added to the reaction mixture over a period of about 60 minutes. A solution of 0.5 molar Rochelle Salt (191 ml) was added to the reaction mixture and the aqueous phase was separated at 40C. The organic phase was washed with 15% w/v brine (3 x 136 ml) and with water (136 ml). The solution was distilled at atmospheric temperature, removing about 400 ml of distillate, with a final distillation temperature of 112C. Triethylenediamine (51.62 g) was added to the reaction mixture followed by tosyl chloride (87.90 g) in toluene (416 ml) over a period of about 60 minutes. Sodium hydroxide (2nu, 160 ml) was added to the reaction mixture and the organic layer separated and washed successively with water (80 ml), citric acid (0.5M, EPO 80 ml) and water (80 ml). The organic phase was concentrated at reduced pressure with a maximum internal temperature of 70C, collecting about 600 ml of distillate. The solution was cooled to 200C and isohexane (160 ml) was added. Once crystallisation had occurred, further isohexane (320 ml) was added. The product was temperature cycled to 40C, the suspension was cooled to 50C and the product was isolated by filtration and dried at 4O0C. Yield: 127.9 g, 86.5 %; NMR Spectrum (CDCl3) 1.0-1.2 (m, 2H), 1.45 (s, 9H), 1.65 (d, 2H), 1.75-1.9 (m, 2H), 2.45 (s, 3H), 2.55-2.75 (m, 2H) 3.85 (d, IH), 4.0-4.2 (br s, 2H), 7.35 (d, 2H), 7.8 (d, 2H); Mass Spectrum [ESI]: (MNa)+ = 392., 123855-51-6

The synthetic route of 123855-51-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/36713; (2007); A2;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem