tert-butyl (2S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(2-fluoro-6-nitrophenoxy)methyl]morpholine-4-carboxylate → tert-butyl (2S,5S)-2-[(2-amino-6-fluorophenoxy)methyl]-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)morpholine-4-carboxylate

Participants

Reaction Steps

Dissolved tert-butyl (2S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(2-fluoro-6-nitrophenoxy)methyl]morpholine-4-carboxylate (1.68 g, 3.36 mmol) in ethyl acetate (11.19 mL) and to this solution, carefully added 10% Pd/C (0.714 g, 0.671 mmol). A hydrogen filled balloon was attached and the contents were evacuated and backfilled with H2 several times. Stirred at room temperature for 4 hours. Complete at this time by LC/MS. The solids were filtered off through a pad of celite and washed with ethyl acetate and ethanol. The contents were concentrated and then purified on silica gel (40 g) eluting with a gradient of 0-90% EtOAc/hexanes afforded the title compound (1.57 g, 3.34 mmol, 100% yield) as a yellow oil,

Provenance & Evidence