Ethyl Acetate → 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol

Participants

Reaction Steps

To a stirred solution of ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (Preparation 50D, 80 mg, 0.153 mmol) in ethanol (1 mL) was added sodium borohydride (30 mg, 0.793 mmol) at room temperature. The reaction mixture was stirred at room temperature for 19 hr before ethyl acetate (4 mL) and water (2 ml) were added followed by the addition of saturated aqueous ammonium chloride solution (3 mL). The aqueous layer was separated and extracted with ethyl acetate (3×2 mL). The combined ethyl acetate solutions were dried over sodium sulfate and concentrated under reduced pressure to give a white solid. The solid was triturated with ethyl acetate to give 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butan-1-ol (32 mg, 0.066 mmol, 43.5% yield) as a white solid.

Provenance & Evidence