Triethylamine → HCID 54428075, compound

Participants

Reaction Steps

Under nitrogen atmosphere to a solution of (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(pyrimidin-5-ylmethyl)pyrrolidine (21.0 g) in dichloromethane (105 ml) were added triethylamine (16.1 g) firstly and methanesulfonyl chloride (13.7 g) secondly at 5° to 10° C. After the reaction mixture was stirred for an hour at the same temperature, dichloromethane (50 ml) and ice-water (150 ml) were added thereto, and then the solution was stirred vigorously for twenty minutes. The organic layer was separated and washed with 1N-hydrochloric acid (100 ml), 1N-sodium hydroxide (200 ml), and brine (200 ml). The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-4-methanesulfonyloxy-2-(pyrimidin-5-ylmethyl) pyrrolidine (25.2 g) as an oil.

Provenance & Evidence