4-Bromobenzoic acid → Pyrrolidine, 1-(4-bromobenzoyl)-2-(1-pyrrolidinylmethyl)-, (2S)-

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Reaction Steps

To a stirring solution of 4-bromobenzoic acid-2,5-dioxo-pyrrolidin-1-yl ester (3.5 g, 11.7 mmol), [which can be prepared from 4-bromobenzoic acid and N-hydroxy succinamide by the method of C. Mitsos, Chem Pharm Bull 48(2), 211-214 (2000), or purchased from Ambinter, CAS# 80586-82-9], in tetrahydrofuran (0.15 M), add (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine and heat to reflux for 4 h. After this time, remove the heat and wash the reaction with water while extracting with 10% isopropanol/dichloromethane. Dry the organic portion with sodium sulfate, filter and concentrate in vacuo. Purify the resulting residue on a silica column eluting with 2 M ammonia in methanol and dichloromethane to give (4-bromo-phenyl)-(2-(S)-pyrrolidin-1-ylmethyl-pyrrolidin-yl)methanone (93% yield with 80% purity). MS (m/e): 337.1 (M+1).

Provenance & Evidence