Sodium borohydride → 1-Benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

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Reaction Steps

To a solution of 1-benzyl-4-(2-methoxy-ethyl)-3-oxo-piperidine-4-carboxylic acid ethyl ester (774 mg, 2.42 mmol) in MeOH (5 mL) at 0° C. was carefully added sodium borohydride (110 mg, 2.91 mmol) and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was quenched with 1N NaOH and diluted with further 1N NaOH and ethyl acetate. The organic layer was separated washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a crude residue which was purified by flash column chromatography to give 1-benzyl-3-hydroxy-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (610 mg, 78%) as a white solid. MS (ESI): 322.3 (MH+).

Provenance & Evidence