Triethylamine → Ammonium hydroxide methanol

Participants

Reaction Steps

To a solution of 1-{[(1S,3R)-3-amino-1-isopropylcyclopentyl]carbonyl}-4-phenylpiperidin-4-ol hydrochloride (50 mg, 0.1 mmol), 3-methoxytetrahydro-4H-pyran-4-one (53 mg, 0.41 mmol), and triethylamine (0.066 mL, 0.48 mmol) in methylene chloride (2 mL) was added sodium triacetoxyborohydride (0.087 g, 0.41 mmol). After being stirred overnight at room temperature, the reaction was quenched with a saturated NaHCO3 solution. 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 17 min. Bottle A=1% NH4OH/2% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded the desired product. MS calculated for C26H40N2O4: (M+H) 445; found 445.2.

Provenance & Evidence