Sodium Cyanide → 1-tert-Butyl 2-methyl (2S,4R)-4-cyanopyrrolidine-1,2-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (4R)-1-(tert-butyloxycarbonyl)-4-(methane-sulfonyloxy)-L-proline methyl ester (2.31 g, 7.14 mmol) and sodium cyanide (3.5 g, 71.4 mmol) in dry dimethylsulfoxide (46 mL) was stirred for 24 hours at 55° C. under a nitrogen atmosphere. The cooled reaction mixture was diluted with ethyl acetate, washed with water (2×), saturated brine solution, dried (MgSO4), and evaporated. The crude product mixture was subjected to flash silica gel chromatography eluting with 15% acetone/hexane. Fractions containing the desired nitrile were combined and evaporated to afford a colorless oil; yield 205 mg (11%).

Provenance & Evidence