Triethylamine → Ammonium hydroxide methanol

Participants

Reaction Steps

To a solution of (1R,3S)-3-isopropyl-3-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]cyclopentanamine hydrochloride (50 mg, 0.1 mmol), 3-methoxytetrahydro-4H-pyran-4-one (56 mg, 0.43 mmol), and triethylamine (0.07 mL, 0.5 mmol) in methylene chloride (2 mL) was added sodium triacetoxyborohydride (91 mg, 0.43 mmol). After being stirred at room temperature overnight, saturated NaHCO3 was added. The solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (gradient: 0-15% B over 15 min. Bottle A=1% NH4OH/3% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded the desired compound. MS calculated for C26H38N2O3: (M+H) 427; found 427.3.

Provenance & Evidence