Triethylamine → (2S,4R)-1-(3-Chloro-benzyl)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester

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Reaction Steps

Chloro-3-chloromethyl-benzene (15.2 ml, 120 mmol) was added to the mixture of 4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (14.5 g, 80 mmol) and triethylamine (18.6 g, 180 mmol) in dichloromethane (120 ml). The reaction mixture was refluxed overnight. After cooling, 1M aqueous sodium hydroxide was added, and the mixture was extracted with dichloromethane. The extract was washed with brine, dried over sodium sulfate, concentrated and purified by chromatography on silica gel (hex/EA=5:1 to hex/EA=31) to give 14 g title product as yellow oil in 65% yield.

Provenance & Evidence