Metaperiodic acid → 21-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-(2-oxo-2-phenylethoxy)pregna-1,4-diene-3,20-dione

HRID 918382Notes

Reaction equation

HRID 918382 reaction equation
[Cl:1][CH2:2][C:3](=[O:38])[C@:4]1([OH:37])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@:18]([F:24])([C@@H:19]([OH:23])[CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:25])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[O:26][CH2:27][C:28]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)C[O:29]1.I(O)(=O)(=O)=O>O1CCCC1.O>[Cl:1][CH2:2][C:3](=[O:38])[C@:4]1([OH:37])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@:18]([F:24])([C@@H:19]([OH:23])[CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:25])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[O:26][CH2:27][C:28](=[O:29])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 65185Metaperiodic acidHCID 8673374621-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-[(2-phenyloxiranyl)methoxy]pregna-1,4-diene-3,20-dione

Product 1

HCID 8673374721-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-(2-oxo-2-phenylethoxy)pregna-1,4-diene-3,20-dioneYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.8 g of 21-chloro-9-fluoro-11β,17-dihydroxy-16α-[(2-phenyloxiranyl)methoxy]pregna-1,4-diene-3,20-dione in 150 ml of tetrahydrofuran is stirred with a solution of 10 g of periodic acid in 40 ml of water for 4 hours. The resulting slurry is diluted with 1 liter of water and filtered. The solid is dried in vacuo and recrystallized from methanol-chloroform to give 2.4 g of 21-chloro-9-fluoro-11β,17-dihydroxy-16α-(2-oxo-2-phenylethoxy)pregna-1,4-diene-3,20-dione, melting point 266°-268°C, dec.

Workup

  1. filtrationfiltered
  2. customThe solid is dried in vacuo
  3. customrecrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-b78d762d08ef4f76b6a29aa8bcf96c57
Source dataset
uspto-grants-1976_07
Patent number
US03971772

Reaction notes

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