Water → HCID 178484027, compound

Participants

Reaction Steps

A solution of 8.16 g (29 mmol) of trans-[4-(3-hydroxy-prop-1-ynyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester in 230 ml methylenechloride was treated at 0° C. with 2.48 ml (31.9 mmol) of methanesulfonylchloride and 5.05 ml (43.5 mmol) of 2,6-lutidine. The reaction mixture was stirred over night to room temperature. The reaction was cooled (0° C.) and treated again with 0.68 ml (8.7 mmol) of methanesulfonylchloride and 1.68 ml (14.5 mmol) of 2,6-lutidine and stirred for 24 hours. Water (35 ml) was added and the reaction was stirred for 5 minutes. After extraction with aqueous saturated NaHCO3/ether (3×), the organic phases were washed with aqueous 10% NaCl, dried over sodium sulfate and evaporated to yield 12.5 g of crude trans-methanesulfonic acid 3-{4-[(tert-butoxycarbonyl-methyl-amino)-methyl]-cyclohexyl}-prop-2-ynyl ester as brown oil, MS: 360 (MH+).

Provenance & Evidence