Acetic Acid → 6'-methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

Participants

Reaction Steps

To a mixture of NaBH4 (1 g) added in portions to a solution of cooled trifluoroacetic acid and acetic acid (30 mL, v/v: 1/1), was added 6′-methoxy-5′,7′-dimethyl-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinolin]-4′-ol in 10 mL THF. After 30 minutes, the reaction mixture was quenched with water and extracted with ethyl acetate (3×20 mL). The organic layer was dried with Na2SO4, evaporated, and purified by column chromatography (1-2% methanol in CH2Cl2), to give 6′-methoxy-5′,7′-dimethyl-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinoline] as a brown oil (500 mg).

Provenance & Evidence