Benzyl Alcohol → HCID 19424454, compound

Participants

Reaction Steps

To a stirred solution of 16.61 ml (191.31 mmol) of chlorosulfonyl isocyanate in methylene chloride was added phenylmethanol (19.92 ml, 191.31 mmol) at 0° C. After stirring the above solution for 2 hours at this temperature, a solution of 30.84 g (182.2 mmol) of ethyl 2-azabicyclo[2,2,1]heptan-3-carboxylate in methylene chloride containing triethylamine (42.92 ml) was added at 0° C. and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 500 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride, the combined organic layer was concentrated in vacuo and purified by flash chromatography (30% ethyl acetate in hexane) to yield 40.75 g (58.5%) of ethyl N-(carbobenzyloxyaminosulfonyl)-2-azabicyclo [2,2,1]-heptan-3-carboxylate (Formula XIV: R=Ethyl; R1 =H; R2 and R3 together = ##STR18## as an oil.

Provenance & Evidence