Reaktion #50728

ord-c05cdbbfbba14f20a453eb4c70efeaa1

Reaktionsgleichung

CCOCC
Ether
[Al+3].[H-].[H-].[H-].[H-].[Li+]
Lithium aluminum hydride
CON(C)C(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C
compound ( 7 )
CON(C)C(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C
[t-Butyloxycarbonyl)-L-Leucine N-Methoxy-N-methylamide
O=S(=O)([O-])O.[K+]
potassium hydrogen sulfate
→
CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C
desired product
CC(C)C[C@@H](C=O)NC(=O)OC(C)(C)C
(t-Butyloxycarbonyl)-L-Leucinal

Edukte

CCOCC
Ether
[Al+3].[H-].[H-].[H-].[H-].[Li+]
Lithium aluminum hydride
CON(C)C(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C
compound ( 7 )
CON(C)C(=O)[C@H](CC(C)C)NC(=O)OC(C)(C)C
[t-Butyloxycarbonyl)-L-Leucine N-Methoxy-N-methylamide
O=S(=O)([O-])O.[K+]
potassium hydrogen sulfate

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe aqueous phase is separated
  2. 2
    Extraktionextracted
  3. 3
    Waschenwashed with 1N HCl saturated sodium hydrogen carbonate and saturated sodium chloride
  4. 4
    Trocknendried with magnesium sulfate
  5. 5
    SonstigeThe solvent is evaporated

Vorschrift

Lithium aluminum hydride (2.5 equiv.) is added to a stirred solution of compound (7). Reduction is complete within 15-20 minutes. The mixture is hydrolyzed with a solution of potassium hydrogen sulfate in water. Ether is added and the aqueous phase is separated and extracted. The organic phases are combined, washed with 1N HCl saturated sodium hydrogen carbonate and saturated sodium chloride, and dried with magnesium sulfate. The solvent is evaporated to leave the desired product

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05428019uspto-grants-1995_06