Acetic Acid → HCID 68670712, compound

Participants

Reaction Steps

CH2O (aq, 37%) (0.12 ml, 0.127 g, 1.56 mmol, 4 eq) was added to a stirred solution of tert-butyl 3-amino-5-methoxybenzylcarbamate (0.0975 g, 0.39 mmol, 1 eq) in 5 ml CH3CN. After 10 min NaBH3CN (0.056 g, 0.897 mmol, 2.3 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc. After stirring overnight the reaction was diluted with Et2O/water and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 (×2), 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 0.0638 g (0.228 mmol, 58% yield) of tert-butyl 3-(dimethylamino)-5-methoxybenzylcarbamate.

Provenance & Evidence