Sodium triacetoxyborohydride → 4-[((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)amino]-1-pyridin-2-ylcyclohexanol

Participants

Reaction Steps

To a solution of 4-hydroxy-4-pyridin-2-yl-cyclohexanone (42.3 mg, 0.221 mmol) of step D-2 and (1R,3S)-3-isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentanamine (103 mg, 0.221 mmol) of Step C-2 in CH2Cl2(8 mL) was added sodium triacetoxyborohydride (200 mg, 1.0 mmol). After being stirred at room temperature overnight, the reaction was quenched with aqueous NaOH. The solution was extracted with CH2Cl2. The organic layer was concentrated in vacuo. The residue was purified via HPLC to provide two diastereomers. Isomer 1: LCMS calculated for C30H38F3N3O2: (M+H)+530; found 530.1. Isomer 2: MS found 530.1.

Provenance & Evidence