Triethylamine → HCID 57938714, compound

Participants

Reaction Steps

To a solution of (1R,3S)-3-isopropyl-3-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)cyclopentanamine bis(trifluoroacetate) (140 mg, 0.23 mmol), 3-methoxytetrahydro-4H-pyran-4-one (90 mg, 0.69 mmol) and triethylamine (0.096 mL, 0.69 mmol) in methylene chloride (10 mL) was added sodium triacetoxyborohydride (97 mg, 0.46 mmol). After being stirred at room temperature overnight, the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3. The aqueous layer was extracted with EtOAc three times. The combined organic layers were dried (MgSO4), concentrated and purified on silica gel eluting with EtOAc to 1% Et3N/EtOAc affording 105 mg (92%) of the desired product. The product was separated by chiral HPLC to give two major isomers. MS calculated for C26H38F3N3O3: (M+H) 498; found 498.2 for both isomers.

Provenance & Evidence