Lithium borohydride → 1-Boc-4-(hydroxymethyl)-4-methylpiperidine

Participants

Reaction Steps

To a mixture of 1-tert-butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (0.10 g, 0.37 mmol) in THF (10 mL) and ethanol (20 mL) was added LiBH4 (0.032 g, 1.5 mmol). The mixture was stirred for about 8 h at rt. The mixture was diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The EtOAc extracts were combined, dried over anhydrous Na2SO4, and concentrated in vacuo to give tert-butyl 4-(hydroxymethyl)-4-methylpiperidine-1-carboxylate (0.067 g, 80%): LC/MS (Table 2, Method i) Rt=0.29 min; MS m/z: 130 (M-Boc+H)+.

Provenance & Evidence