6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,10a-hexahydro-phenanthrene → 6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418955노트

반응식

HRID 418955 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13]([CH3:17])=[C:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[H][H]>[Pd].C(O)(=O)C.CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH3:17])[CH:12]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

참가 물질

5

반응물 2

HCID 666520386-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,10a-hexahydro-phenanthreneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 666519736-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene수율 93%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 18673759MeOH THF HOAc용매

실험 절차

Combine 6-methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,10a-hexahydro-phenanthrene (0.116 g, 0.347 mmol), Pd-Black (14.7 mg, 0.139 mmol) and acetic acid/methanol/tetrahydrofuran (1.0 mL, 10.0 mL, 3.0 mL) at 50 psi Hydrogen pressure. After 18 hours, filter off the Pd catalyst over celite eluting with ethyl acetate. Concentrate and flash chromatograph with 0% to 10% ethyl acetate/hexanes to yield the titled compound (0.108 g, 93%) as a clear oil. TLC Rf=0.30 in 5:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.26 (d, 1H, J=8.4 Hz), 7.03 (m, 3H), 6.83 (m, 3H), 3.90 (s, 3H), 3.83 (s, 3H), 3.36 (m, 2H), 3.12 (m, 1H), 2.52 (m, 1H), 2.35 (m, 1H), 1.87 (m, 1H), 1.51 (m, 4H), 1.30 (m, 2H), 1.18 (d, 3H, J=6.6 Hz).

후처리

  1. filtrationfilter off the Pd catalyst over celite
  2. washeluting with ethyl acetate
  3. concentrationConcentrate

출처 및 근거

ORD 기록
ord-7e842b54ec34499998abc1e5be7b152e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093302B2

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