Triethylamine → HCID 15537965, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-hydroxypropyl)pyrrolidine (17.1 g) in dichloromethane (170 ml) were added successively triethylamine (10.4 ml) and methanesulfonyl chloride (4.63 ml) under an ice-bath. The mixture was stirred at 0° C. for 1.5 hours and quenched by the addition of water (85 ml). The aqueous layer was separated and extracted with dichloromethane (50 ml×2). The organic layers were combined and washed with 1N hydrochloric acid (85 ml), brine (85 ml) and dried over magnesium sulfate. Evaporation of the solvent gave (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(3-methanesulfonyloxypropyl)pyrrolidine (21.2 g) as a yellow paste.

Provenance & Evidence