Water → 8-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-ol

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Reaction Steps

Add sodium borohydride (2.60 g, 0.0688 mol) portionwise over 15 minutes to a stirred suspension of 8-chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one (15.0 g, 0.0573 mol) in methanol (150 mL) at 25°-35° C. and under an atmosphere of nitrogen. Stir the mixture for 40 minutes at 25°-30° C. Concentrate the mixture in vacuo to provide a suspension, and then pour it into water (150 mL), and extract with CH2Cl2 (3×100 mL). Combine the extracts, wash with water (3×75 mL), dry over Na2SO4, filter, and concentrate in vacuo. Purify the crude product (18.4 g) via flash chromatography by eluting with EtOAc/hexanes (1:1) to obtain the title compound (9.70 g, 64% yield).

Provenance & Evidence