Acetic Acid → HCID 68669887, compound

Participants

Reaction Steps

CH2O (aq. 37%, 1.57 mL, 21.1 mmol, 10 eq) was added to a stirred solution of tert-butyl 3-aminobenzylcarbamate (0.47 g, 2.1 mmol, 1 eq) in 10 mL CH3CN. The resulting solution was treated with NaBH3CN (0.42 g, 6.3 mmol, 3 eq) followed by the dropwise addition of HOAc to pH=7. The solution was stirred for 1 h adding HOAc occasionally to keep the pH close to 7. The reaction was concentrated in vacuo and the resulting residue was diluted with sat. NaHCO3 and extracted into EtOAc (×1). The organic layer was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent removed in vacuo. Purification via flash chromatography on silica gel yielded 0.39 g (1.6 mmol, 74% yield) of tert-butyl 3-(dimethylamino)benzylcarbamate.

Provenance & Evidence