t-Butyl 5-fluoro-4-hydroxy-3-nitropentanoate → 3-Amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester

To a solution of t-butyl 5-fluoro-4-hydroxy-3-nitropentanoate (950 mg, 4.0 mmol) in MeOH (20 mL) was added Raney Ni (about 200 mg), the mixture was shaken under H2 (30-35 psi) at rt for 18 h. It was filtered and the catalyst was washed with MeOH (2×10 mL). The MeOH solution was evaporated and the residue was purified by chromatography over silica gel (EtOAc-MeOH, 10:1) to give 840 mg (96%) of the titled compound as a yellowish viscous oil. 1HNMR (CDCl3), 1.450 (s, 9H), 2.12 (bs, 3H, OH and NH2), 2.28-2.38 (m, 1H), 2.47-2.57 (m, 1H), 3.24-3.30 (m, 1H), 3.54-3.76 (m, 1H), 4.38-4.48 (m, 1H), 4.54-4.61 (m, 1H).

1. filtrationIt was filtered
2. washthe catalyst was washed with MeOH (2×10 mL)
3. customThe MeOH solution was evaporated
4. customthe residue was purified by chromatography over silica gel (EtOAc-MeOH, 10:1)

ORD record

ord-cef629289e464f3f8bdfda377f2dd4d9

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949516B2