Methanol → HCID 13990935, compound

HRID 1658705Notes

Reaction equation

HRID 1658705 reaction equation
C([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C@@H:22]([F:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:25])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[F:24][C@H:22]1[CH2:23][C@@:6]2([CH3:7])[C@@H:8]([CH2:9][CH2:10][C@@H:5]2[OH:4])[C@H:11]2[C@H:21]1[C@:19]1([CH3:20])[C:14]([CH2:13][CH2:12]2)=[CH:15][C:16](=[O:25])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 68147202HCID 68147202, compound

Product 1

HCID 13990935HCID 13990935, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.2 g. of 17β-acetoxy-11β-fluoro-4-androsten-3-one is stirred in a mixture of 30 ml. of methanol and 5 ml. of water for 10 hours at room temperature with 1 g. of potassium carbonate. The reaction mixture is filtered off from the insoluble matter, the solution is neutralized with glacial acetic acid, concentrated under vacuum, the residue taken up in methylene chloride, and dried. After recrystallization from acetone/hexane, 800 mg. of 11β-fluoro-17β-hydroxy-4-androsten-3-one is obtained; m.p. 161°-162°. UV: ε239 = 16,600 (methanol).

Workup

  1. filtrationThe reaction mixture is filtered off from the insoluble matter
  2. concentrationconcentrated under vacuum
  3. customdried
  4. customAfter recrystallization from acetone/hexane, 800 mg

Sources & evidence

ORD record
ord-b1b914fd1e3b48b79b3434dd10d782f0
Source dataset
uspto-grants-1976_06
Patent number
US03966713

Reaction notes

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