Dimethylformamide → HCID 69597614, compound

Participants

Reaction Steps

A solution of (1R,4R)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXVI, 10 mmol) and dimethylformamide (20 ml) at about 0° C. was treated with triethylamine (10–20 mmol) and 4-benzyloxybenzenesulfonyl chloride (15 mmol). After stirring for about 1 hours, the mixture is warmed to a temperature of about 20° C. to about 25° C. and stirred for about an additional 12 hours. The mixture is diluted with 1M hydrochloric acid, extracted twice with ethyl acetate, and the combined organic layers are dried over sodium sulfate, filtered and concentrated in vacuo to give (1R,4R)-5-(4-benzyloxy-benzenesulfonyl)-8,8-dimethyl-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one as a colorless syrup.

Provenance & Evidence