Ethyl 6-methoxy-1H-indole-2-carboxylate → Rac-6-methoxy-2,3-dihydro-1h-indole-2-carboxylic acid ethyl ester

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Sodium cyanoborohydride (750 mg, 12 mmol) (Aldrich) was added in small portions to a mixture of 6-Methoxy-1H-indole-2-carboxylic acid ethyl ester (500 mg, 2.4 mmol) (Aldrich) in TFA (10 mL), which was cooled in ice-water bath, at such a rate that gas evolution was not too vigorous. When the addition was complete, the mixture was allowed to warm to room temperature and stirred for 2.5 hr. The resulting mixture was concentrated in vacuo and the residue was dissolved in DCM. The organic layer was washed with Na2CO3 solution, dried with Na2SO4, and concentrated to give 400 mg rac-6-Methoxy-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester. MS: [M+H]+=222

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