HCID 11624650, compound → HCID 54293704, compound

HRID 2058438Notes

Reaction equation

HRID 2058438 reaction equation
[N+:1](=[C:3]1[C:23](=[O:24])[CH2:22][CH2:21][C@@:20]2([CH3:25])[C@H:4]1[CH2:5][CH2:6][C@@H:7]1[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:26])[C@H:8]1[CH2:9][CH2:10][C@@H:11]2[C@@H:12]([CH3:15])[CH2:13][OH:14])=[N-:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[N+:1](=[C:3]1[C:23](=[O:24])[CH2:22][CH2:21][C@@:20]2([CH3:25])[C@H:4]1[CH2:5][CH2:6][C@@H:7]1[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:26])[C@H:8]1[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH:13]=[O:14])[CH3:15])=[N-:2]

Participants

5

Reactant 2

HCID 11624650HCID 11624650, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 54293704HCID 54293704, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. filtrationfiltered through a small column of silica gel in ether
  2. customEvaporation of the solvent
  3. customleaves a solid which
  4. customis recrystallized from ether

Sources & evidence

ORD record
ord-68538c3f8f6f414a81b07709ee8d86bb
Source dataset
uspto-grants-1982_03
Patent number
US04317817

Reaction notes

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