HCID 86616779, compound → HCID 68803424, compound

Participants

Reaction Steps

10% palladium on carbon (30 mg) was added to a solution of 3-azido-1-(cyclopropylmethyl)-5-phenylazepan-2-one (0.3 g, 1.05 mmol) in methanol (4 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 18 h, the reaction was filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→93% dichloromethane/7% (10% ammonium hydroxide/methanol)] gave the title compound (60 mg). The racemic product was resolved on a chiralpak AS (250×20 mm) column using 20% propanol/hexanes→50% propanol/hexanes (0.1% diethylamine in hexanes) to give four enantiomerically pure isomers. MS 259 (M+1).

Provenance & Evidence