Metaperiodic acid → HCID 68128587, compound

HRID 267908Notes

Reaction equation

HRID 267908 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][CH:28]4[CH2:30]O4)[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([CH3:32])[CH2:4][CH2:5][C:6](=[O:31])[CH:7]=1.I(O)(=O)(=O)=O>O1CCCC1.O.ClCCl>[CH2:27]([O:26][C@@H:14]1[CH2:13][C@@H:12]2[C@:20]([CH3:24])([CH2:21][C@H:22]([OH:23])[C@@:2]3([F:1])[C@H:11]2[CH2:10][CH2:9][C:8]2[C@:3]3([CH3:32])[CH2:4][CH2:5][C:6](=[O:31])[CH:7]=2)[C@@:15]1([OH:25])[C:16](=[O:19])[CH2:17][OH:18])[CH:28]=[CH2:30]

Participants

6

Reactant 2

HCID 65185Metaperiodic acidHCID 88831561HCID 88831561, compound

Product 1

HCID 68128587HCID 68128587, compoundYield 22.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20.1 g of crude 9-fluoro-11β ,17,21-trihydroxy-16α-(oxiranyl-methoxy)pregn-4-ene-3,20 -dione, 21-acetate in 300 ml of tetrahydrofuran is stirred with a solution of 30 g of periodic acid in 75 ml of water for 6 3/4 hours. The solution is diluted with water and extracted with chloroform. The chloroform extract was washed with 5% sodium bicarbonate solution, dried, and evaporated in vacuo to give 18.2 g of crude product. This material is dissolved in 60 ml of dichloromethane and chromatographed on a 450 g-silica gel column. Fractions of 250 ml are collected as the column is eluted with 3 liters of dichloromethane, 3 liters of chloroform, and then 3 liters of 19:1 chloroform-ethyl acetate. Fractions 17-21 are combined and evaporated in vacuo to give 4.4 g of 16α-allyloxy-9-fluoro-11β ,17,21-trihydroxypregn-4-ene-3,20-dione, 21-acetate.

Workup

  1. extractionextracted with chloroform
  2. extractionThe chloroform extract
  3. washwas washed with 5% sodium bicarbonate solution
  4. customdried
  5. customevaporated in vacuo
  6. customto give 18.2 g of crude product
  7. customchromatographed on a 450 g-silica gel column
  8. customFractions of 250 ml are collected as the column
  9. washis eluted with 3 liters of dichloromethane, 3 liters of chloroform
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-ffb8a590775644709e79850f6ced1c00
Source dataset
uspto-grants-1976_03
Patent number
US03945997

Reaction notes

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