Acetic Acid → Tert-butyl 3-(benzyl(methyl)amino)benzylcarbamate

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Reaction Steps

CH2O (aq, 37%) (0.112 ml, 0.12 g, 1.51 mmol, 2 eq) was added to a stirred solution of tert-butyl 3-(benzylamino)benzylcarbamate (0.2353 g, 0.753 mmol, 1 eq) in 5 ml CH3CN. After 10 min NaBH3CN (0.0615 g, 0.98 mmol, 1.3 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc. After 2 h the solvent was removed in vacuo. The residue was diluted with saturated aqueous NaHCO3/EtOAc, and the layers were separated. The organic layer was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo to yield 0.2482 g (0.76 mmol, 100% yield) of tert-butyl 3-(benzyl(methyl)amino)benzylcarbamate.

Provenance & Evidence