Acetic Acid → (3aR,4R,5R,6aS)-4-((R)-3-Hydroxy-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol
Reaktionsgleichung
[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]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 45 °C
Versuchsvorschrift
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.
Aufarbeitung
- extractionthe product was extracted with dichloromethane (3×20 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (elution with gradient ethyl acetate/hexane from 1:2 to 3:1 v/v)
Quellen und Nachweise
- ORD-Eintrag
- ord-d06e9afb6d9947949531e0f30b3afa13
- Quelldatensatz
- uspto-grants-2005_08
- Patentnummer
- US06927300B2
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