Sodium Hydroxide → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirred mixture of 22.2 g (193 mmol) of 4-hydroxymethylpiperidine in 100 mL of CH2Cl2 and 75 mL of a 15% solution of NaOH was added a solution of 63.2 g (289 mmol) of BOC2O in 50 mL of CH2Cl2 over 2 h. After stirring for a further 30 min, the reaction mixture was extracted with 15% NaOH solution and sat'd Nacl solution. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ehtyl acetate, 19:1, then 4:1, then 1:1) to give 25 g of the title compound.

Provenance & Evidence