Sodium borohydride → HCID 66958239, compound

Participants

Reaction Steps

Sodium borohydride (77 mg, 2.0 mmol) was added portionwise to a stirred suspension of 6′-bromospiro[cyclohexane-1,3′-indoline]-2′,4-dione (preparation 21a, 0.30 g, 1.0 mmol) in methanol (14 mL) at room temperature. After 2.5 hours the mixture was concentrated in vacuo and water was added. The mixture was extracted with ethyl acetate and the organic layer was dried (MgSO4) and evaporated to give the title compound as a mixture of isomers. Separation of the isomers was achieved by reverse phase chromatography (C-18 silica from Waters©, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 60%) to give, in order of elution, the pure minor isomer as a white solid (0.075 g, 25%):

Provenance & Evidence