Sodium borohydride → Tert-butyl 4-(6-hydroxymethyl-pyridin-3-yl)-piperazine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-(6-formyl-pyridin-3-yl)-piperazine-1-carboxylate (0.39 mmol) in THF (10 mL) is added NaBH4 (2.72 mmol) and the reaction mixture is stirred at room temperature for 1 hour. After it is cooled to 0° C., the reaction mixture is slowly mixed with ice cold water (5 mL) and then partitioned between saturated Na2CO3 solution and 10% MeOH in EtOAc. The aqueous phase is extracted with 10% MeOH in EtOAc. The combined organic extracts are washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (100/10/1 EtOAc/MeOH/Et3N) to give tert-butyl 4-(6-hydroxymethyl-pyridin-3-yl)-piperazine-1-carboxylate.

Provenance & Evidence