Triethylamine → Ammonium hydroxide methanol

Participants

Reaction Steps

To a solution of (1R,3S)-3-isopropyl-3-{[4-[2-(trifluoromethyl)phenyl]-3,6-dihydropyridin-1(2H)-yl]carbonyl}cyclopentanamine hydrochloride (46 mg, 0.11 mmol), tetrahydro-4H-pyran-4-one (33 mg, 0.33 mmol), and triethylamine (0.054 mL, 0.39 mmol) in methylene chloride (2 mL) was added sodium triacetoxyborohydride (70 mg, 0.33 mmol). After being stirred overnight at room temperature, a saturated NaHCO3 solution was added. The resulting solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0-20% B over 15 min. Bottle A=1% NH4OH/2% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) provided the desired product. MS calculated for C26H35F3N2O2: (M+H) 465; found 465.2.

Provenance & Evidence