Triethylamine → (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine

Participants

Reaction Conditions

Reaction Steps

A mixture of L-hydroxyproline methyl ester hydrochloride (the compound obtained in Reference Example 1-1); 24.37 g, 134 mmol) and triethylamine (41.2 ml, 295 mmol) in methylene chloride (240 ml) was stirred at room temperature for 10 minutes, cooled to -5° C., treated dropwise with a solution of allyl chloroformate (14.9 ml, 140 mmol) in methylene chloride (30 ml). The reaction mixture was stirred at -5° C. for 1 hour, and washed twice with water. The organic layer was dried over anhydrous sodium sulfate and evaporated to afford the title compound (30.8 g, 100% yield) as an oil.

Provenance & Evidence