HCID 89922359, compound → HCID 89923237, compound

Participants

Reaction Steps

Zinc (107 mg, 1.630 mmol) was added to a mixture of (S)-4-chloro-3-((4-(2,4-dimethoxybenzyl)morpholin-3-yl)methoxy)-5-nitrobenzonitrile (isomer B, 73 mg, 0.163 mmol) and ammonium chloride (174 mg, 3.26 mmol) in methanol (5 mL) and the reaction mixture was stirred at room temperature for 2 hours. More zinc (107 mg, 1.630 mmol) was added and stirring continued until reactions complete. The reaction mixture was diluted with dichloromethane and ammonium chloride precipitated. Solids were filtered and the filtrate was concentrated. The residue was partitioned between dichloromethane and saturated sodium bicarbonate. The layers were separated and aqueous layer was extracted with dichloromethane two more times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (12 g column, eluting with 5-35% ethyl acetate/hexanes) to give (S)-3-amino-4-chloro-5-((4-(2,4-dimethoxybenzyl)morpholin-3-yl)methoxy)benzonitrile (53 mg) as a oil.

Provenance & Evidence