Sodium borohydride → Tert-butyl 3,4-bis(hydroxymethyl)piperidine-1-carboxylate

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Reaction Steps

To a mixture of 1-tert-butyl 3,4-dimethyl piperidine-1,3,4-tricarboxylate (4.00 g, 13.30 mmol, 1 eq) in 50 mL of anhydrous EtOH was added NaBH4 (1.26 g, 33.20 mmol, 2.5 eq) in portions at 0° C. The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was purified by a silica gel column chromatography (5:1 (v/v) CH2Cl2/MeOH) to afford the title compound as a white solid (3.00 g, 92.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 246.2 (M+1).

Provenance & Evidence