Benzyl Alcohol → HCID 86749822, compound

Participants

Reaction Steps

To a stirred solution of 3.01 ml (34.72 mmol) of chlorosulfonyl isocyanate in 200 ml of dry methylene chloride was added phenylmethanol (3.61 ml, 34.72 mmol) at 0° C. After stirring the above solution for 1 hour at this temperature, a solution of 7.3 g (33.07 mmol) of methyl 3-propyl-piperidine-2-carboxylate hydrochloride in methylene chloride containing triethylamine (13.75 ml; 99.21 mmol) was added at 0° C., and the resulting mixture was stirred overnight (17 hours) allowing the mixture to warm to room temperature. The reaction mixture was diluted with the same volume of methylene chloride and 200 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride and the combined organic layer was washed with brine, dried and concentrated in vacuo. The residual oil was purified by flash chromatography (30% ethyl acetate in hexane) to yield 11.43 g (86.7%) of N-(carbobenzyloxyaminosulfonyl)-3-propyl-2-piperidinecarboxylic acid methyl ester(Formula XIV: R=CH3;R1 =H; R2 and R3 together =-[CH(propyl)(CH2)3 ]-) as an oil.

Provenance & Evidence