Trifluoromethanesulfonic acid → HCID 45100641, compound

HRID 861644Notes

Reaction equation

HRID 861644 reaction equation
[CH3:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][C@H:10](OS(C(F)(F)F)(=O)=O)[C:11]2=[O:21])[CH2:3]1.C[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3C[C@@H](O)C2=O)C1.FC(F)(F)S(O)(=O)=O.[Cl-:60].[Li+]>CN(C=O)C.O>[CH3:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][C@@H:10]([Cl:60])[C:11]2=[O:21])[CH2:3]1

Participants

7

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 433294Lithium ChlorideHCID 18637647HCID 18637647, compoundHCID 86743737HCID 86743737, compound

Product 1

HCID 45100641HCID 45100641, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

800 mg of 3β-methyl-16β-trifluoromethylsulfonyloxy-5-androsten-17-one, prepared from 3β-methyl-16α-hydroxy-5-androsten-17-one and trifluoromethane sulfonic acid was placed in 16 ml DMF and was treated with 100 mg Lithium chloride at room temperature. The reaction mixture was stirred magnetically for 21 hours. Water is then added and the resulting crystalline ppt was collected. The crystals were washed with additional water and were then dissolved in CH2Cl2, filtered through anhydrous sodium sulfate and the solvent was evaporated off. The resulting crystals were recrystallized from CH3OH, yielding 570 mg of final product. m.p. 159°-165° C.

Workup

  1. customthe resulting crystalline ppt was collected
  2. washThe crystals were washed with additional water
  3. dissolutionwere then dissolved in CH2Cl2
  4. filtrationfiltered through anhydrous sodium sulfate
  5. customthe solvent was evaporated off
  6. customThe resulting crystals were recrystallized from CH3OH

Sources & evidence

ORD record
ord-850d024d96b34fc1ba80cdec131913b1
Source dataset
uspto-grants-1998_02
Patent number
US05714481

Reaction notes

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