Benzyl {2-[(tert-butoxycarbonyl)amino]-3-(dimethylamino)-3-oxopropyl}carbamate → 3-amino-N2-(tert-butoxycarbonyl)-N,N-dimethylalaninamide

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Reaction Conditions

Reaction Steps

To a solution of benzyl {2-[(tert-butoxycarbonyl)amino]-3-(dimethylamino)-3-oxopropyl}carbamate (5.5 g, 15 mmol) in methanol (100 mL) was added palladium on carbon (0.55 g, 10% w/w). The reaction mixture was stirred under a hydrogen (50 psi) atmosphere at 50° C. After 4 hours, the reaction mixture was filtered and concentrated under reduced pressure to afford 3-amino-N2-(tert-butoxycarbonyl)-N,N-dimethylalaninamide. MS ESI calc'd. for C10H22N3O3 [M+H]+ 232. found 232. 1H NMR (400 MHz, CD3OD) δ 4.59-4.46 (m, 1H), 2.91 (s, 3H), 2.86 (s, 3H), 2.75-2.72 (m, 1H), 2.71-2.69 (m, 1H) 1.43 (s, 9H).

Provenance & Evidence