Potassium Carbonate → (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopentane-1,2-dicarboxylic acid monoethyl ester

HRID 1367485

Reaktionsgleichung

Reaktionsgleichung von HRID 1367485
C([Si]([O:8][C:9]([C@@H:11]1[CH2:15][CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:13][C@H:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:10])(C)C)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O1CCCC1.O>[CH2:27]([O:26][C:24]([C@@H:12]1[CH2:13][CH:14]([O:16][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:18])[CH3:19])[CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:25])[CH3:28]

Komponenten

6

Edukt 2

HCID 11430Potassium CarbonateHCID 59619369(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopentane-1,2-dicarboxylic acid 1-ethyl ester 2-(tert-Butyl-dimethyl-silanyl) Ester

Produkt 1

HCID 59619299(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopentane-1,2-dicarboxylic acid monoethyl esterAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopentane-1,2-dicarboxylic acid 1-ethyl ester 2-(tert-Butyl-dimethyl-silanyl) Ester (epimeric mixture, 12.09 g) in ethanol (340 mL) and tetrahydrofuran (114 mL) was slowly added a solution of potassium carbonate (16.68 g) in water (114 mL). After 45 min at room temperature, the solvents were removed in vacuo. Brine was added to the residue and the mixture was cooled to 0° C. then the pH was adjusted to 4-5 using a 10% aqueous solution of potassium hydrogenosulfate. The resulting mixture was extracted with diethylether. The combined organic layers were washed with brine then dried over sodium sulfate and concentrated in vacuo to afford the title compound (8.03 g, 90%) as light yellow oil, used in the next step without further purification. MS (EI): 315.2 (M−H)−.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. additionBrine was added to the residue
  3. extractionThe resulting mixture was extracted with diethylether
  4. washThe combined organic layers were washed with brine
  5. dry with materialthen dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6883a42e9d6e4e86a1b2d18581f8061a
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893099B2

Verknüpfte Notizen

Wird geladen…