Acetic Acid → (3aR,4R,5R,6aS)-4-((R)-3-Hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

HRID 584886노트

반응식

HRID 584886 반응식
[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][CH:7]([OH:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([O:22]C1CCCCO1)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C1COCC1.[OH-].[K+]>O>[OH:1][C@@H:2]1[CH2:10][C@@H:5]2[O:6][CH:7]([OH:9])[CH2:8][C@@H:4]2[C@H:3]1[CH2:11][CH2:12][C@@H:13]([OH:22])[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 10110977(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(3R)-5-phenyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]pentyl]-2H-cyclopenta[b]furan-2-ol

생성물 1

HCID 10425274(3aR,4R,5R,6aS)-4-((R)-3-Hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol수율 43%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
45 °C

실험 절차

A mixture of compound [11a] (0.55 g), acetic acid (2 ml), THF (2 mL) and water (2 mL) was stirred at 40-50° C. for 4 hours (TLC monitoring). The mixture was basified with 1 N aq. potassium hydroxide to pH 10-11 and the product was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v) to give 0.18 g (43%) of the compound [11b] as a colorless oil. 1H NMR (CD3OD) is compatible with literature data.

후처리

  1. extractionthe product was extracted with dichloromethane (3×20 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v)

출처 및 근거

ORD 기록
ord-d06e9afb6d9947949531e0f30b3afa13
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927300B2

반응 노트

불러오는 중…