Water → Ammonium Hydroxide

Participants

Reaction Steps

To 155a (1.0003 g, 3.8 mmol) dissolved in acetone (20 mL) was added a solution of cycloheptylamine (0.5 mL, 3.8 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.5 mL, 3.8 mmol) and water (4 mL). The reaction mixture was allowed to stir at reflux for 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over sodium sulfate. The filtered sample was concentrated on the rotary evaporator and the resulting solid was dried overnight under vacuum. Flash column chromatography (SiO2, 90:9:1 dichloromethane:methanol:conc. ammonium hydroxide) yielded a white solid (155b, 856 mg, 66%), mp>210° C.; HPLC: Inertsil ODS-3V C18, 40:10:50 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 10.0 min, 96.0% purity; MS (TOF MS ES+): m/z 342 (51.5), 341 (35.1), 340 (M+H, 100).

Provenance & Evidence