Sodium Bicarbonate → 3-[2-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-(hydroxymethyl)-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide

Participants

Reaction Steps

Sodium borohydride (0.804 g) was added to a stirred solution of 3-[2-(3-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpropyl)-4-formyl-1-oxo-1,2-dihydroisoquinolin-6-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide (Example 26f, 8 g) in ethanol (80 mL) at room temperature under nitrogen. After 5 min, saturated aqueous NaHCO3 (40 mL) was added and the mixture extracted with ethyl acetate (100 mL). The organic layer was washed with water (40 mL), dried (Na2SO4), filtered and evaporated. The residue was purified (SiO2 chromatography, elution with 5-50% ethyl acetate in isohexane) to give the subtitle compound (5.72 g) as a solid.

Provenance & Evidence