Sodium Hydroxide → (2S,3S)-3-(5-(1-Cyanocyclopropyl)-2-methoxybenzyl)amino-2-phenylpiperidine

Participants

Reaction Steps

To a stirred suspension of Compound 3 (150 mg, 0.60 mmol) and Compound 2 (145 mg, 0.72 mmol) in dry CH2Cl2 (5 ml) was added NaBH(OAc)3 (358 mg, 1.68 mmol) portionwise at room temperature. The reaction mixture was stirred at room temperature for 6 h. The mixture was basified to pH10-11 with 10% NaOH aq. with ice-cooling. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product. The crude product (300 mg) was purified by column chromatography on silica gel with CH2Cl2 -MeOH (20:1-10:1) to give Compound 4 (89 mg, 41%) as a yellow viscous oil.

Provenance & Evidence