HCID 13190202, compound → HCID 13190205, compound

HRID 1388652Notes

Reaction equation

HRID 1388652 reaction equation
C([O:4][CH2:5][C:6](=[O:32])[C@@:7]12[O:31][CH2:30][O:29][C@@H:8]1[CH2:9][C@@H:10]1[C@:24]2([CH3:25])[CH2:23][C@H:22]([OH:26])[C@@:21]2([F:27])[C@H:11]1[CH2:12][CH2:13][C:14]1[C@:19]2([CH3:20])[CH:18]=[CH:17][C:16](=[O:28])[CH:15]=1)(=O)C>Cl(O)(=O)(=O)=O.CO.C(Cl)Cl>[F:27][C@:21]12[C@@H:22]([OH:26])[CH2:23][C@@:24]3([CH3:25])[C@@H:10]([CH2:9][C@H:8]4[O:29][CH2:30][O:31][C@:7]43[C:6](=[O:32])[CH2:5][OH:4])[C@@H:11]1[CH2:12][CH2:13][C:14]1[C@:19]2([CH3:20])[CH:18]=[CH:17][C:16](=[O:28])[CH:15]=1

Participants

5

Reactant 1

HCID 13190202HCID 13190202, compound

Product 1

HCID 13190205HCID 13190205, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 24247Perchloric AcidSolvent

Procedure

18.0 g of 21-acetoxy-9α-fluoro-11β-hydroxy-16α,17α-methylenedioxy-1,4-pregnadiene-3,20-dione is stirred in a mixture of 216 ml of 60% perchloric acid and 720 ml of methanol at room temperature for 18 hours. The reaction solution is diluted with methylene chloride and poured on water. After extraction with methylene chloride, neutralizing, washing, drying, and concentration of the organic extracts, 14.0 g of a crude product is obtained which is recrystallized from hexane/acetone, yielding 10.6 g of 9α-fluoro-11β,21-dihydroxy-16α,17α-methylenedioxy-1,4-pregnadiene-3,20-dione, mp 262° C.

Workup

  1. additionpoured on water
  2. extractionAfter extraction with methylene chloride
  3. washwashing
  4. customdrying
  5. customconcentration of the organic extracts, 14.0 g of a crude product is obtained which
  6. customis recrystallized from hexane/acetone

Sources & evidence

ORD record
ord-dab729c16019409facf3ab4fa444deb0
Source dataset
uspto-grants-1984_02
Patent number
US04432976

Reaction notes

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