2-{[(Tert-butoxy)carbonyl](methyl)amino}-2-methylpropanoic acid → tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)-N-methylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of N-(tert-butoxycarbonyl)-N,2-dimethylalanine in THF (0.17 M) was treated at RT with BH3-DMS complex in THF (10 eq., 2M) and the mixture was stirred at 45° C. for 8 h. The reaction was carefully quenched with H2O and the pH adjusted to 9 with 2M aq. Na2CO3. The mixture was then extracted with EtOAc and washed with brine. After drying over Na2SO4, the crude material was purified by FC (10-50% EtOAc in PE) to afford the product. (ES+) m/z 204 (M+H)+.

Provenance & Evidence