Dichloromethane → (2S,4S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution (3S,5S)-5-(3-chloro-2-fluoro-benzylcarbamoyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (550 mg, 1.33 mmol) in THF (6 mL) was added lithium borohydride (2 M in THF, 1.46 mL, 2.92 mmol) at RT and the mixture was further stirred for 2 h under N2 atmosphere. After completion brine and CH2Cl2 were added, the layers were separated and the aqueous one re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4), filtered and concentrated. The crude was purified by flash column chromatography on silica gel (eluent: EtOAc) to give the desired material. MS (LC/MS): 409.1 [M+Na]+, 287.0 [MH−Boc]+, 385.1 [M−H]−; tR (HPLC conditions f): 1.82 min.

Provenance & Evidence