Acetic Acid → Tert-butyl 3-(diethylamino)benzylcarbamate

Participants

Reaction Conditions

Reaction Steps

Acetaldehyde (0.52 ml, 0.4 g, 9.08 mmol, 5 eq) was added to a stirred solution of tert-butyl 3-aminobenzylcarbamate (derived from 3-(aminomethyl)aniline (TCI America)) in 11 ml CH3CN/H2O (10:1) at 0° C. After 5 min NaBH3CN (0.3 g, 4.54 mmol, 2.5 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc and stirred at 0° C. for 5 min. The ice-bath was removed and the reaction was stirred at room temperature for 45 min. The solvent was removed in vacuo. The residue was diluted with saturated aqueous NaHCO3 and extracted with EtOAc (×2). The combined organics were washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.3875 g (1.4 mmol, 77% yield) of tert-butyl 3-(diethylamino)benzylcarbamate.

Provenance & Evidence