Water → HCID 131716312, compound

HRID 466510Notes

Reaction equation

HRID 466510 reaction equation
[CH3:1][C:2]1[CH2:21][C@@H:20]2[C@:7]([CH3:27])([CH2:8][CH2:9][C@H:10]3[C@H:19]2[CH2:18][CH:17]=[C:16]2[C@:11]3([CH3:26])[CH2:12][CH2:13][C@H:14]([O:22][C:23](=[O:25])[CH3:24])[CH2:15]2)[C:3]=1[C:4](=O)[CH3:5].Cl.[NH2:29][OH:30].O>C(O)C.N1C=CC=CC=1>[CH3:1][C:2]1[CH2:21][C@@H:20]2[C@:7]([CH3:27])([CH2:8][CH2:9][C@H:10]3[C@H:19]2[CH2:18][CH:17]=[C:16]2[C@:11]3([CH3:26])[CH2:12][CH2:13][CH:14]([O:22][C:23](=[O:25])[CH3:24])[CH2:15]2)[C:3]=1[C:4](=[N:29][OH:30])[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 7091834982-06-9

Product 1

HCID 131716312HCID 131716312, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

A solution of 16-methyl-3β-acetoxy-5,16-pregnadien-20-one (3.70 g, 10 mmoles) was refluxed in a mixture of ethanol (100 ml) and pyridine (10 ml) containing 3.50 g (50 mmoles) of hydroxylamine hydrochloride for one hour. The reaction mixture was added to water and the crude product was filtered and washed with water. Solution in methylene chloride, filtration through anhydrous sodium sulfate, and concentration to dryness in vacuo gave the crude oxime.

Workup

  1. filtrationthe crude product was filtered
  2. washwashed with water
  3. filtrationSolution in methylene chloride, filtration
  4. concentrationthrough anhydrous sodium sulfate, and concentration to dryness in vacuo

Sources & evidence

ORD record
ord-24f83d73e3e4438c90f82a9d20b79db3
Source dataset
uspto-grants-1992_10
Patent number
US05157031

Reaction notes

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