Metaperiodic acid → HCID 68128660, compound

HRID 267905Notes

Reaction equation

HRID 267905 reaction equation
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([O:26][CH2:27][C:28]4(C)[CH2:30][O:29]4)[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:33])[CH2:4][CH2:5][C:6](=[O:32])[CH:7]=1.I(O)(=O)(=O)=O>O1CCCC1.O.C(Cl)(Cl)Cl>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([O:26][CH2:27][C:28](=[O:29])[CH3:30])[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:33])[CH2:4][CH2:5][C:6](=[O:32])[CH:7]=1

Participants

6

Reactant 2

HCID 65185Metaperiodic acidHCID 86733170HCID 86733170, compound

Product 1

HCID 68128660HCID 68128660, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.54 g of 9-fluoro-11β ,17,21-trihydroxy-16α-[(2-methyl-oxiranyl)methoxy]pregn-4-ene-3,20-dione, 21-acetate in 50 ml of tetrahydrofuran is stirred for 270 minutes with a solution of 2.6 g of periodic acid in 20 ml of water. The solution is poured into water and extracted with chloroform. The chloroform solution is washed with 10% sodium bicarbonate solution, dried, and evaporated in vacuo to give an oily residue. This is dissolved in chloroform and chromatographed on a 40 g-silica gel column. Elution with chloroform gives 400 mg of slightly impure product followed by 990 mg of TLC homogeneous solid. The 990 mg is recrystallized twice from acetone-hexane to give 328 mg of 9-fluoro-11β ,17,21-trihydroxy-16α-(2-oxopropoxy)pregn-4-ene-3,20-dione, 21-acetate, melting point 203°-208°C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution is washed with 10% sodium bicarbonate solution
  3. customdried
  4. customevaporated in vacuo
  5. customto give an oily residue
  6. customchromatographed on a 40 g-silica gel column
  7. washElution with chloroform
  8. customgives 400 mg of slightly impure product
  9. customThe 990 mg is recrystallized twice from acetone-hexane

Sources & evidence

ORD record
ord-4014441c959c4f328c51cdce42c99f78
Source dataset
uspto-grants-1976_03
Patent number
US03945997

Reaction notes

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