HCID 15713362, compound → HCID 15713356, compound

HRID 373042Notes

Reaction equation

HRID 373042 reaction equation
[OH:1][C@@:2]12[CH2:8][C@@H:7]1[CH2:6][C@H:5]1[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:3]21[CH3:4])[C:17]1[CH2:16][CH2:15][C:14](=[O:21])[CH2:13][C:12]=1[CH2:11][CH2:10]3>N1C=CC=CC=1>[OH:1][C@@:2]12[CH2:8][C@@H:7]1[CH2:6][C@H:5]1[C@H:9]3[C:18]([CH2:19][CH2:20][C@:3]21[CH3:4])=[C:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3

Participants

3

Reactant 1

HCID 15713362HCID 15713362, compound

Product 1

HCID 15713356HCID 15713356, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.3 g of 17beta-hydroxy-16alpha,17alpha-methylene-estr-5(10)-en-3-one is dissolved in 20 ml of pyridine dried on KOH and is mixed at -30° C. with stirring in an inert gas atmosphere with 2.88 g of pyridine hydrobromide perbromide. Then, it is stirred for about 15 minutes at a temperature of about -5° C. and then the excess bromation agent is destroyed by addition of dihydropyrane. Then, it is stirred for 4 hours at room temperature, the reaction mixture is mixed with water and the steroid is extracted with methylene chloride. After the concentration of the extracts by evaporation, the remaining residue is chromatographed on silica gel. A benzene/ethyl acetate mixture (5:1 to 2:1) is used as mobile phase. 1.6 g of dienone, which can be crystallized from aqueous methanol, is obtained.

Workup

  1. customdried on KOH
  2. additionis mixed at -30° C.
  3. stirringThen, it is stirred for about 15 minutes at a temperature of about -5° C.
  4. customthe excess bromation agent is destroyed by addition of dihydropyrane
  5. stirringThen, it is stirred for 4 hours at room temperature
  6. additionthe reaction mixture is mixed with water
  7. extractionthe steroid is extracted with methylene chloride
  8. customAfter the concentration of the extracts by evaporation
  9. customthe remaining residue is chromatographed on silica gel
  10. custom1.6 g of dienone, which can be crystallized from aqueous methanol
  11. customis obtained

Sources & evidence

ORD record
ord-b179be242f9b4fa38d2e34c402313119
Source dataset
uspto-grants-1992_11
Patent number
US05162312

Reaction notes

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