2,2,2-Trifluoro-1-(4-hydroxy-5-nitro-10-aza-tricyclo(6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone → 2,2,2-Trifluoro-1-(4-hydroxy-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7), 3,5-trien-10-yl)-ethanone

HRID 457435

반응식

HRID 457435 반응식
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[C:10]([N+:18]([O-])=O)[C:11]([OH:17])=[CH:12][C:13]=32)[CH2:6]1)=[O:4]>CO.[Pd]>[F:22][C:2]([F:1])([F:21])[C:3]([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[C:10]([NH2:18])[C:11]([OH:17])=[CH:12][C:13]=32)[CH2:6]1)=[O:4]

참가 물질

4

반응물 1

HCID 218647282,2,2-Trifluoro-1-(4-hydroxy-5-nitro-10-aza-tricyclo(6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone

생성물 1

HCID 218647172,2,2-Trifluoro-1-(4-hydroxy-5-amino-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7), 3,5-trien-10-yl)-ethanone

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

2,2,2-Trifluoro-1-(4-hydroxy-5-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone (575 mg, 1.82 mmol) was hydrogenated in methanol under a H2 atmosphere at (45 psi, or approximately 3 atmospheres) over 10% Pd/C (80 mg) for 1.5 hours then filtered through a Celite pad and concentrated to white solids (450 mg, 86%). (TLC 5% methanol/CH2Cl2 (NH3) Rf 0.6). 1H NMR (400 MHz, CD3O)6.67–6.59 (m, 2H), 4.12 (m, 1H), 3.73 (m, 1H), 3.73 (m, 1H), 3.51 (m, 1H), 3.07 (m, 2H), 2.24 (m, 1H), 1.94 (d, J=10.5 Hz, 1H). GCMS m/e 286 (M+).

후처리

  1. filtrationthen filtered through a Celite pad
  2. concentrationconcentrated to white solids (450 mg, 86%)

출처 및 근거

ORD 기록
ord-405dbab13c0f4925a9a2e676797a788d
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186870B2

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