Bromoacetonitrile → 3-Hydroxy-1-pyrrolidineacetonitrile

Participants

Reaction Steps

The method follows that of S3 using 3-hydroxypyrrolidine (15 g, 0.172 mol), BrCH2CN (22.67 g, 0.189 mmol) and dry THF (60 mL). The title-compound was yielded as a straw-coloured oil (15.39 g, 71%) after flash chromatography using CH2Cl2/CH3OH (9:1) as eluent. δH (250 MHz; CDCl3); 1.9-2.25 (m, 2H, 2×ring-H), 2.3 (m, 1H, ring-H), 2.65 (d, OH), 2.85-3.05 (m, 3H, 3×ring-H), 3.95 (d, 2H, NCH2CN) and 4.2 (m, 1H, CH2CHOH); FAB MS, m/z (M+H)+ 127.

Provenance & Evidence