Sodium Chloride → HCID 69317052, Verbindung

HRID 2114840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114840
[CH:1]([C:3]1([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6][CH2:5][CH2:4]1)=O.[O:16]([C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:17][O:16][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1[CH2:20][NH:21][CH2:1][C:3]1([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

8

Edukt 5

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 16217741tert-Butyl (1-formylcyclopentyl)carbamate

Produkt 1

HCID 69317052HCID 69317052, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 1-formylcyclopentylcarbamate (1.87 g, 8.78 mmol) in anhydrous THF (9 mL) was added 2,4-dimethoxylbenzylamine (1.98 mL, 13.17 mmol). The reaction was stirred for 10 min, treated with sodium triacetoxyborohydride (2.98 g, 14.04 mmol), and stirred for an additional 2 h at room temperature under an atmosphere of nitrogen. Saturated aqueous NaHCO3 solution was added and the mixture stirred until gas evolution ceased. The mixture was diluted with EtOAc, and the separated aqueous layer was saturated with NaCl and extracted into EtOAc once more. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo to afford the product.

Aufarbeitung

  1. stirringstirred for an additional 2 h at room temperature under an atmosphere of nitrogen
  2. stirringthe mixture stirred until gas evolution
  3. extractionextracted into EtOAc once more
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford the product

Quellen und Nachweise

ORD-Eintrag
ord-b4dda52a205342519029fc0bb30dea31
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435735B2

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