Dimethyl Sulfoxide → HCID 57485795, compound

Participants

Reaction Conditions

Reaction Steps

A solution of oxalyl chloride (1.31 mL, 15 mmol) in 50 mL of dichloromethane was cooled in a dry ice-acetone bath, and DMSO (1.4 mL, 20 mmol) was added drop-wise over 5 min. After 10 min, ethyl 6-hydroxy-3-azabicyclo[3.3.1]nonane-3-carboxylate (2.2 g, 10 mmol) in 10 mL dichloromethane was added over 5 min. The mixture was stirred for 20 min, and then triethylamine (6.3 mL, 45 mmol) was added slowly. The mixture was stirred for 1.5 h, gradually warming to −10° C. The reaction was quenched by addition of water (25 mL). The organic layer was separated, washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a yellow oil. This was chromatographed on a silica gel column, with 2% methanol in dichloromethane, to give the desired ketone (1.0 g, 45%). The chromatography also provided a sample of the isomeric ketone, ethyl 7-oxo-3-azabicyclo[3.3.1]nonane-3-carboxylate, and some un-reacted alcohol starting material.

Provenance & Evidence