Dimethyl Sulfoxide → Benzyl [(1r,2r)-2-formylcyclohexyl]carbamate

Participants

Reaction Steps

A solution of oxalyl chloride (2.6 mL, 29.4 mmol) in dichloromethane (80 mL) at −78° C. was treated with a solution of dimethyl sulfoxide (4.3 mL, 60.8 mmol) in dichloromethane (10 mL) over 5 minutes. The mixture was stirred for 40 min, then treated with a solution of benzyl[(1R,2R)-2-(hydroxymethyl)cyclohexyl]carbamate (5.0 g, 19 mmol) in dichloromethane (20 mL) over 5 minutes. The mixture was stirred for 45 minutes, then was treated with triethylamine (8.6 mL, 61.7 mmol) and allowed to warm to room temperature. After 60 minutes, the mixture was washed with water, then with brine, and dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography using 30% ethyl acetate in hexane to provide a white solid (4.8 g, 97%).

Provenance & Evidence