Sodium borohydride → HCID 18998207, compound

Participants

Reaction Steps

To a solution of Example D (8.5 g, 30 mmol) in MeOH (80 mL) was slowly added solid NaBH4 (3.42 g, 90 mmol) while the reaction temperature was controlled below 20° C. After stirring for 2 h, the reaction was quenched with H2O, extracted with EtOAc (3×100 mL) and the combined organic layers were washed with brine, dried (Na2SO4), concentrated in vacuo. The residue was purified via flash column chromatography to yield methyl 4-(((t-butoxycarbonyl)methylamino)methyl)benzoate (6.55 g, 77% yield). 1H NMR (CDCl3) δ 7.98 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 3.90 (s, 3H,) 3.84 (s, 2H) 3.29 (s, 2H) 1.46 (s, 9H).

Provenance & Evidence