HCID 67640328, compound → HCID 67640683, compound

Participants

Reaction Steps

A solution (4S)-1-(tert-butyloxycarbonyl)-4-cyano-L-proline tert-butyl ester (470 mg, 1.59 mmol) in 90% ethanol (22 mL) was hydrogenated in the presence of 10% palladium-on-charcoal (225 mg) at 450 psi for 24 hours. The catalyst was removed by filtration through Celite, the filter washed with ethanol, and the combined filtrate and washings evaporated. Purification was achieved by flash silica gel chromatography eluting with 95:5:0.5 chloroform-methanol-ammonia; yield 284 mg (60%). 400 MHz 1H NMR (CD3OD): δ1.41-1.48 (3s, 18H); 1.58 (m, 1H); 2.28 (m, 1H); 2.48 (m, 1H); 2.66 (m, 2H); 3.05 (dd, 1H); 3.71 (dd, 1H); 4.12 (m, 1H).

Provenance & Evidence