Water → HCID 70626946, compound

HRID 1283726Notes

Reaction equation

HRID 1283726 reaction equation
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][CH:14]=[C:15]3[C:16](=[O:19])[CH2:17]I)[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:26])[CH:4]=[CH:5][C:6](=[O:25])[CH:7]=1.S(=O)(O)[O-].[Na+].O>O1CCOCC1>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][CH:14]=[C:15]3[C:16](=[O:19])[CH3:17])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:26])[CH:4]=[CH:5][C:6](=[O:25])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665763Sodium BisulfiteHCID 86733851HCID 86733851, compound

Product 1

HCID 70626946HCID 70626946, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.8 g of 9-fluoro-21-iodo-11β-hydroxypregna-1,4,16-triene-3,20-dione in 135 ml of dioxane is stirred with 90 ml of 5% sodium bisulfite at 105°C under nitrogen for 1.5 hours. The solution is cooled, poured into water, stirred for 30 minutes and filtered. The solid is washed with water and dried in a vacuum oven at 60°C over phosphorous pentoxide to give 780 mg of material. Crystallization from chloroform-methanol gives 420 mg of the title compound, melting point 327°-328°C.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. washThe solid is washed with water
  4. dry with materialdried in a vacuum oven at 60°C over phosphorous pentoxide

Sources & evidence

ORD record
ord-f6db2abfe91e41898383721d4b5a35c2
Source dataset
uspto-grants-1976_08
Patent number
US03976638

Reaction notes

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