Formaldehyde → (R)-tert-butyl 3-(hydroxymethyl)-4-methylpiperazine-1-carboxylate

Participants

Reaction Steps

To a solution of (R)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (115 mg, 0.53 mmol) in acetonitrile (1.4 mL) and water (0.3 mL) was added Formalin (0.11 mL, 1.6 mmol) followed by sodium triacetoxyborohydride (225 mg, 1.1 mmol). The reaction mixture was stirred for 20 minutes at ambient temperature. The reaction mixture was then basified via the addition of saturated aqueous sodium carbonate solution (1 mL), diluted with methylene chloride (50 mL) and methanol (5 mL), and washed with saturated aqueous sodium bicarbonate solution (2×15 mL). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo to afford a white crystalline solid, which was used in the next step without any further purification (120 mg, 98%).

Provenance & Evidence