Triamcinolone → 9-Fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione

HRID 1585479Notes

Reaction equation

HRID 1585479 reaction equation
[CH3:1][C@@:2]12[C@@:10]([OH:15])([C:11]([CH2:13][OH:14])=[O:12])[C@H:9]([OH:16])[CH2:8][C@H:7]1[C@@H:6]1[CH2:17][CH2:18][C:19]3[C@@:25]([CH3:26])([C@@:5]1([F:27])[C@@H:4]([OH:28])[CH2:3]2)[CH:24]=[CH:23][C:21](=[O:22])[CH:20]=3>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH3:26][C@@:25]12[C@@:5]3([F:27])[C@@H:4]([OH:28])[CH2:3][C@:2]4([CH3:1])[C@@:10]([OH:15])([C:11]([CH2:13][OH:14])=[O:12])[C@H:9]([OH:16])[CH2:8][C@H:7]4[C@@H:6]3[CH2:17][CH2:18][C:19]1=[CH:20][C:21](=[O:22])[CH2:23][CH2:24]2

Participants

5

Reactant 1

HCID 31307Triamcinolone

Product 1

HCID 2287859-Fluoro-11beta,16alpha,17,21-tetrahydroxypregn-4-ene-3,20-dione

Reagents, catalysts & solvents 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A suspension of 3.0 g of tris(triphenylphosphine)rhodium chloride in 1000 ml of degassed toluene was hydrogenated for 45 min at room temperature and atmospheric pressure. A solution of 5.0 g of triamcinolone in 500 ml of absolute ethanol was added and the hydrogenation was continued for 48 h. The reaction mixture was evaporated to dryness and suspended in 50 ml of methylene chloride. After filtration the solid phase was repeatedly washed with small portions of methylene chloride and yielded after drying 4.4 g of 9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione. Molecular weight 396 (calc. 396.5).

Workup

  1. waitthe hydrogenation was continued for 48 h
  2. customThe reaction mixture was evaporated to dryness
  3. filtrationAfter filtration the solid phase
  4. washwas repeatedly washed with small portions of methylene chloride
  5. customyielded
  6. dry with materialafter drying 4.4 g of 9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione

Sources & evidence

ORD record
ord-12d5e8139c61486b81b47158dbc0c6ac
Source dataset
uspto-grants-1999_08
Patent number
US05939409

Reaction notes

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