Dimethylformamide → 9-(4-Hydroxy-phenyl)-10-methoxymethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol

HRID 418970노트

반응식

HRID 418970 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][O:18][CH3:19])[CH:12]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.C([S-])C.[Na+].CN(C=O)C>C(OCC)(=O)C>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([CH:12]2[CH:13]([CH2:17][O:18][CH3:19])[C:14]3[CH:15]=[CH:16][C:3]([OH:2])=[CH:4][C:5]=3[CH:6]3[CH:11]2[CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 4459711Sodium ethanethiolateHCID 666519026-Methoxy-9-methoxymethyl-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

생성물 1

HCID 666519829-(4-Hydroxy-phenyl)-10-methoxymethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol수율 33%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Combine 6-methoxy-9-methoxymethyl-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (0.050 g, 0.14 mmol), sodium ethanethiolate (0.037 g, 0.44 mmol), and DMF (4 mL), and reflux under nitrogen atmosphere. After 18 hours, cool the reaction to room temperature and add ethyl acetate, wash with sat ammonium chloride solution (aq), then brine several times. Concentrate, and purify using reverse phase chromatography (5% to 95% 0.001% TFA buffer in acetonitrile/water) to yield the titled compound (0.015 g, 33%) as a white solid. TLC Rf=0.27 in 3:1 hexanes:ethyl acetate. 1H NMR (d-methanol): 7.42 (d, 1H, J=8.4 Hz), 7.13 (d, 2H, J=8.4 Hz), 6.84 (s, 1H), 6.79 (d, 2H, J=8.4 Hz), 6.65 (dd, 1H, J=7.9, 1.8 Hz), 3.70 (d, 1H, J=7.0 Hz), 3.35 (m, 3H), 3.17 (s, 3H), 3.07 (m, 1H), 2.48 (d, 1H, J=14.1 Hz), 1.87 (m, 1H), 1.64 (m, 2H), 1.41 (m, 2H), 1.16 (m, 3H).

후처리

  1. temperaturecool
  2. customthe reaction to room temperature
  3. washwash with sat ammonium chloride solution (aq)
  4. concentrationConcentrate
  5. custompurify

출처 및 근거

ORD 기록
ord-ba9f58d2808e4da498f3448912bbe0b5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093302B2

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