(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

HRID 243231노트

반응식

HRID 243231 반응식
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH3:12])[NH:7][C:6]=2[C:5]([N+:13]([O-])=O)=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]([CH3:12])[NH:7][C:6]=2[C:5]([NH2:13])=[CH:4][CH:3]=1

참가 물질

4

반응물 1

HCID 68158225(S)-8-Fluoro-3-methyl-5-nitro-3,4-dihydro-2H-benzo[1,4]oxazine

생성물 1

HCID 68158155(S)-8-Fluoro-3-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-5-ylamine수율 102.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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)

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-4b8014f5a3a249f5abf4f9d24f53ab6a
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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