Reaktion #2145620

ord-68538c3f8f6f414a81b07709ee8d86bb

Reaktionsgleichung

C[C@@H](CO)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C(=[N+]=[N-])C(=O)CC[C@]4(C)[C@H]3CC[C@]12C
(5α,20R)-4-diazo-21-hydroxy-20-methyl-pregnane-3-one
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
→
C[C@@H](C=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C(=[N+]=[N-])C(=O)CC[C@]4(C)[C@H]3CC[C@]12C
(5α,20R)-4-diazo-3-oxopregnane-20-carboxaldehyde

Edukte

C[C@@H](CO)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C(=[N+]=[N-])C(=O)CC[C@]4(C)[C@H]3CC[C@]12C
(5α,20R)-4-diazo-21-hydroxy-20-methyl-pregnane-3-one
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate

Reagenzien

Keine

Lösungsmittel

CCOCC
ether
ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered through a small column of silica gel in ether
  2. 2
    SonstigeEvaporation of the solvent
  3. 3
    Sonstigeleaves a solid which
  4. 4
    Sonstigeis recrystallized from ether

Vorschrift

To 60 mg of (5α,20R)-4-diazo-21-hydroxy-20-methyl-pregnane-3-one in 5 ml of dichloromethane is added 60 mg of pyridinium chlorochromate and the mixture is stirred for 16 hours at room temperature. It is then diluted with ether and filtered through a small column of silica gel in ether. Evaporation of the solvent leaves a solid which is recrystallized from ether to give (5α,20R)-4-diazo-3-oxopregnane-20-carboxaldehyde which melts with decomposition.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04317817uspto-grants-1982_03