HCID 9904438, compound → 17beta-Hydroxy-14alpha,15alpha-methylene-androsta-1,4-diene-3-one

HRID 49760Notes

Reaction equation

HRID 49760 reaction equation
[OH:1][C@H:2]1[CH2:7][C@@H:6]2[CH2:8][C@:5]32[C@H:9]2[C@H:19]([CH2:20][CH2:21][C@:3]13[CH3:4])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]2>C1(C)C=CC=CC=1>[OH:1][C@H:2]1[CH2:7][C@@H:6]2[CH2:8][C@:5]32[C@H:9]2[C@H:19]([CH2:20][CH2:21][C@:3]13[CH3:4])[C@:17]1([CH3:18])[C:12](=[CH:13][C:14](=[O:22])[CH:15]=[CH:16]1)[CH2:11][CH2:10]2

Participants

3

Reactant 1

HCID 9904438HCID 9904438, compound

Product 1

HCID 1551334017beta-Hydroxy-14alpha,15alpha-methylene-androsta-1,4-diene-3-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

17β-Hydroxy-14α,15α-methylene-androst-4-ene-3-one (4 g) in 160 mL of toluene is stirred for 6 days at 85° C. with 3.2 g of 2,3-dichloro-5-6-dicyanobenzoquinone. The precipitate is filtered off, washed with a little toluene and the filtrates and washings are evaporated to dryness. The residue is purified by chromatography, 17β-Hydroxy-14α,15α-methylene-androsta-1,4-diene-3-one being obtained.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with a little toluene
  3. customthe filtrates and washings are evaporated to dryness
  4. customThe residue is purified by chromatography, 17β-Hydroxy-14α,15α-methylene-androsta-1,4-diene-3-one being
  5. customobtained

Sources & evidence

ORD record
ord-8d836a3a984f4b898185746876ee0868
Source dataset
uspto-grants-2004_03
Patent number
US06710039B1

Reaction notes

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