Sodium Cyanide → HCID 67640328, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4R)-1-(tert-butyloxycarbonyl)-4-(methane-sulfonyloxy)-L-proline tert-butyl ester (680 mg, 1.86 mmol) and sodium cyanide (912 mg, 18.6 mmol) in N,N-dimethylformamide (14 mL) was stirred for 16 hours at 80° C. under a nitrogen atmosphere. The cooled reaction mixture was diluted with ethyl acetate (100 mL), washed with water (2×), saturated brine solution, dried (Na2SO4), and evaporated. The crude product mixture was subjected to flash silica gel chromatography eluting with 20% ethyl acetate/hexane. Fractions containing the TLC less-mobile isomer were combined and evaporated to afford the desired title compound; yield 275 mg (50%). 400 MHz 1H NMR (CDCl3): δ1.42-1.48 (4s, 18H); 2.24 (m, 1H); 2.67 (m, 1H); 3.08 (m, 1H); 3.64 (m, 1H); 3.81-3.96 (m, 1H); 4.17-4.28 (m, 1H).

Provenance & Evidence