Triethylamine → 1-({(1S,3R)-1-Isopropyl-3-[(3-methoxytetrahydro-2H-pyran-4-yl)amino]cyclopentyl}carbonyl)-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol

Participants

Reaction Steps

To a solution of 1-{[(1S,3R)-3-amino-1-isopropylcyclopentyl]carbonyl}-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol hydrochloride (50 mg, 0.1 mmol), 3-methoxytetrahydro-4H-pyran-4-one (45 mg, 0.34 mmol), and triethylamine (0.048 mL, 0.34 mmol) in methylene chloride (2 mL) was added sodium triacetoxyborohydride (0.073 g, 0.34 mmol). After being stirred overnight at room temperature, a saturated solution of 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 (0-20% B over 15 min. Bottle A=1% NH4OH/2% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded 15 mg of the desired product as an oil. MS calculated for C27H39F3N2O4: (M+H) 513; found 513.2.

Provenance & Evidence