Sodium borohydride → tert-butyl (3R,4S)-3-fluoro-4-hydroxypiperidine-1-carboxylate

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Reaction Steps

To a stirred solution of tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate (1.3 g, 6.0 mmol) in methanol (15 mL), NaBH4 (0.29 g, 7.7 mmol) was added at 0° C. and stirred for 2-3 h. Methanol was removed in vacuo and the residue was diluted with ethyl acetate and washed with water. The organic layer was separated, concentrated in vacuo and the residue was purified by flash column chromatography to give cis(±)-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate (0.850 g, 65%) and trans(±)-tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate (0.315 g, 24%); MS: 242.1 (M+23).

Provenance & Evidence