Sodium borohydride → tert-Butyl 2-(hydroxymethyl)-6-phenylpyridin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1E (2.37 g, 7.94 mmol) in THF (10 mL) and ethanol (20 mL) at 0° C. was added sodium borohydride (300 mg, 7.94 mmol) in several portions. After addition, the reaction was stirred at 0° C. for 10 min, and no starting material was detected by LC-MS. The resultant mixture was quenched with saturated aqueous NaHCO3 (30 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with saturated NaCl, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (120 g) column chromatography eluting with a isocratic of 15% EtOAc in hexane to give the title compound as a white solid (2.25 g, 95%). LC/MS (method A): retention time=3.06 min, (M+H)+=301.

Provenance & Evidence