Potassium bisulfate → tert-Butyl (1-formylcyclopentyl)carbamate

HRID 2114839Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114839
CON(C)[C:4]([C:6]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+]>C1COCC1.O.CCOCC>[CH:4]([C:6]1([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5]

Komponenten

7

Edukt 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 86612118HCID 86612118, Verbindung

Produkt 1

HCID 16217741tert-Butyl (1-formylcyclopentyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of tert-butyl 1-{[methoxy(methyl)amino]carbonyl}-cyclopentylcarbamate (3.34 g, 12.27 mmol) in anhydrous THF (112 mL) at 0° C. under an atmosphere of nitrogen was added LAH (698 mg, 18.40 mmol), portionwise. The reaction was stirred at 0° C. for 30 min, treated with KHSO4 (3.4 g) in water (72 mL), diluted with Et2O, and stirred for 5 min. The layers were separated, and the aqueous was extracted with Et2O three times more. The combined organic extracts were washed twice each with aqueous 1N HCl solution, saturated aqueous NaHCO3 solution, and brine, dried over MgSO4, and concentrated in vacuo to afford the product as a sticky solid.

Aufarbeitung

  1. stirringstirred for 5 min
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with Et2O three times more
  4. washThe combined organic extracts were washed twice each with aqueous 1N HCl solution, saturated aqueous NaHCO3 solution, and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d69914b860444c10984f8737faca2aac
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435735B2

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