(S)-8-Fluoro-3-methyl-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine → (S)-8-Fluoro-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamine

Participants

Reaction Steps

A suspension of (S)-8-fluoro-3-methyl-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine (183 mg, 0.86 mmol) and 10% Pd/C (37 mg) in EtOAc (12 mL) and IMS (1.2 mL) was stirred under a H2 balloon for 16 h. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to give the title compound as a pale yellow oil (160 mg, quant.). 1H NMR (CDCl3, 300 MHz): δ 6.35 (1H, dd, J=10.8, 8.6 Hz), 6.14 (1H, dd, J=8.6, 4.6 Hz), 4.19 (1H, dd, J=10.5, 2.9 Hz), 3.64 (1H, dd, J=10.5, 8.4 Hz), 3.43 (1H, dqd, J=8.4, 6.5, 2.9 Hz), 3.10 (3H, br s), 1.17 (3H, d, J=6.5 Hz)

Provenance & Evidence