Reaktion #343998

ord-83e78408960341df9e98dbcf9734e612

Reaktionsgleichung

O=S(=O)([O-])O.[K+]
KHSO4
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CC(C)(C)OC(=O)N(CC(=O)O)C1CCCCC1
BOC-CYCLOHEXYLGLYCINE
→
CC(C)(C)OC(=O)N(CC=O)C1CCCCC1
BOC-CYCLOHEXYLGLYCINAL

Edukte

O=S(=O)([O-])O.[K+]
KHSO4
—
solution
[Al+3].[H-].[H-].[H-].[H-].[Li+]
LiAlH4
CC(C)(C)OC(=O)N(CC(=O)O)C1CCCCC1
BOC-CYCLOHEXYLGLYCINE

Reagenzien

Keine

Lösungsmittel

O
H2O
CCOCC
Et2O
CCOCC
Et2O

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe mixture was filtered through Celite
  2. 2
    Waschenwashed with 10% citric acid and saturated NaHCO3
  3. 3
    SonstigeAfter drying the solvent
  4. 4
    Sonstigewas removed under reduced pressure

Vorschrift

A solution of 40 g (0.119 mole) of BOC-CYCLOHEXYLGLYCINE, O,N-DIMETHYLHYDROXAMIDE in 550 ml Et2O was cooled in ice and 148 ml (0.148 mole) of a 1M solution of LiAlH4 in Et2O added over 0.5 hour. After an additional 15 minutes, the mixture was treated cautiously with 28 g of KHSO4 in 100 ml H2O. The mixture was filtered through Celite and washed with 10% citric acid and saturated NaHCO3. After drying the solvent was removed under reduced pressure to give the crude BOC-CYCLOHEXYLGLYCINAL. The material was used immediately in the following reaction. ##STR175##

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05260278uspto-grants-1993_11