(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S,E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate → (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate

HRID 245599노트

반응식

HRID 245599 반응식
[C:1]([O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][C@H:13]1[CH2:22][C@@H:21]([OH:23])[C@H:20](/[CH:24]=[CH:25]/[C@@H:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C@H:14]1[CH2:15]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[C:1]([O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][C@H:13]1[CH2:22][C@@H:21]([OH:23])[C@H:20]([CH2:24][CH2:25][C@@H:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C@H:14]1[CH2:15]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 1

HCID 72204417(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S,E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate

생성물 1

HCID 72204610(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate수율 87%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S,E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate (0.35 g, 0.8 mmol) in dry methanol (2.5 ml) was treated with 5% Pd/C (0.05 g, 20% wt) and stirred under hydrogen for 5 hours at room temperature. Then, the reaction mixture was filtered with celite pad. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield: 87%.

후처리

  1. filtrationThen, the reaction mixture was filtered with celite pad
  2. customThe solvent was evaporated off under vacuum
  3. customThe crude product was purified by chromatography on silica gel using
  4. additiona mixture of hexane and ethyl acetate as a gradient eluent

출처 및 근거

ORD 기록
ord-d26c8f6d8c5f468b9abe2d7b75cb0e6b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658837B2

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