(2S,5S)-tert-butyl 5-[(carbamoyloxy)methyl]-2-[(2-fluoro-6-nitrophenoxy)methyl]morpholine-4-carboxylate → (2S,5S)-tert-butyl 2-[(2-amino-6-fluorophenoxy)methyl]-5-[(carbamoyloxy)methyl]morpholine-4-carboxylate

Participants

Reaction Steps

A solution of the product from step 4 (1.4 g, 3.3 mmol) was dissolved in ethyl acetate (50 mL) and the solution was de-gassed with a stream of nitrogen for 10 min. To the degassed solution was added 5% palladium on charcoal (400 mg), and the mixture was stirred under a hydrogen atmosphere at ambient pressure for 16 h. The catalyst was removed by filtration through a celite pad, and the filter cake was washed with CH2Cl2 (200 mL). The filtrate solvents were removed under reduced pressure. The residue was purified on a 12 g SiO2 column using 20-50% EtOAc in hexanes to provide the product (700 mg) as a white solid. LC MS: RT=3.49 min, M+H=400 (6 min gradient).

Provenance & Evidence