(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide → tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

HRID 78738

Reaktionsgleichung

Reaktionsgleichung von HRID 78738
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([O:11][C:12]([NH:14][C@H:15]([C:20](N(C)OC)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])([CH3:10])[CH3:9]>CCOCC>[CH:20]([C@@H:15]([NH:14][C:12](=[O:13])[O:11][C:8]([CH3:7])([CH3:10])[CH3:9])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:21]

Komponenten

4

Edukt 2

HCID 11119284(S)-N-methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of LiAlH4 (0.356 g, 9.38 mmol) in Et2O (20 mL) at 0° C. was added dropwise a solution of N2-{[(1,1-dimethylethyl)oxy]carbonyl}-N1-methyl-N1-(methyloxy)-L-leucinamide (2.34 g, 8.53 mmol) in Et2O (15 mL). The reaction mixture was stirred for 30 min at 0° C. and quenched with EtOAc (6 mL) followed by 5% aq. potassium bisulfate (6 mL). The reaction mixture was washed with 1 M aq. HCl (2×10 mL), saturated aq. NaHCO3 (2×10 mL), and brine (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound as a clear, colorless oil.

Aufarbeitung

  1. customquenched with EtOAc (6 mL)
  2. washThe reaction mixture was washed with 1 M aq. HCl (2×10 mL), saturated aq. NaHCO3 (2×10 mL), and brine (10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-49fd62e9f4714c8d841a596f58bd85e6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841463B2

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