Benzyl Alcohol → N-(carbobenzyloxyaminosulfonyl)-2-piperidine-carboxylic acid methyl ester

Participants

Reaction Steps

To a stirred solution of 7.36 ml (85 mmol) of chlorosulfonyl isocyanate in 180 ml of methylene chloride was added phenylmethanol (8.82 ml, 85 mmol) at 0° C. over a period of 35 minutes. After stirring the above solution for 2 hours at this temperature, a solution of 16.65 g (93 mmol) of 2-piperidinecarboxylic acid methyl ester hydrochloride in methylene chloride (500 ml) containing triethylamine (35.3 ml) was added at 0°-5° C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride (2×200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 31 g of N-(carbobenzyloxyaminosulfonyl)-2-piperidinecarboxylic acid methyl ester(Formula XIV: R=CH3 ; R1 =H; R2 and R3 together =-(CH2)4-) as a solid.

Provenance & Evidence