Potassium Carbonate → (3aR,4R,5R,6aS)-4-[(t-Butyldiphenylsiloxy)methyl]-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one

HRID 275754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275754
C([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@@H:11]1[CH2:19][O:20][Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CO.[Cl-].[Na+].O>[O:20]([CH2:19][C@H:11]1[C@@H:12]2[C@@H:13]([O:14][C:15](=[O:17])[CH2:16]2)[CH2:18][C@H:10]1[OH:9])[Si:21]([C:34]([CH3:35])([CH3:36])[CH3:37])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 22951116(3aR,4R,5R,6aS)-5-Benzoyloxy-4-[(t-butyldiphenylsiloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one

Produkt 1

HCID 22951115(3aR,4R,5R,6aS)-4-[(t-Butyldiphenylsiloxy)methyl]-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-oneAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 3 (15.7 g, 30.0 mmol) in methanol (100 mL) was added potassium carbonate (4.14 g, 30.0 mmol). After 1 h, saturated ammonium chloride (100 mL) and saturated brine (100 mL) were added, the mixture was extracted with methylene chloride (3×100 mL), dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 15 cm tall×41 mm diameter silica gel column eluting with 40% ethyl acetate in hexane to afford 4 (9.93 g, 79%).

Aufarbeitung

  1. extractionthe mixture was extracted with methylene chloride (3×100 mL)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on a 15 cm tall×41 mm diameter silica gel column
  6. washeluting with 40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-18f16e9d4b4b4930816c32edfbbe4552
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353000B1

Notizen zur Reaktion

Wird geladen…