p-Toluenesulfonic acid monohydrate → HCID 70145156, compound

HRID 840184Notes

Reaction equation

HRID 840184 reaction equation
C1CO[C:3]2([CH:8]=[CH:7][C@H:6]3[C@H:9]4[C@H:19]([CH2:20][CH2:21][C@:4]23[CH3:5])[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([OH:22])[CH2:15][CH2:16]2)=[CH:11][CH2:10]4)[O:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[OH:22][CH:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:12](=[CH:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:5])[C@H:6]3[CH:7]=[CH:8][C:3]2=[O:2])[CH2:13]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11034899HCID 11034899, compound

Product 1

HCID 70145156HCID 70145156, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

17,17-Ethylenedioxy-androst-5,15(16)-dien-3β-ol from Example 28B or otherwise obtained is dissolved in acetone (500 mL) and water (60 mL) and the solution is cooled to 0° C. To the 0° C. solution is added p-toluenesulfonic acid monohydrate (1.000 g, 5.257 mmol). The 0° reaction mixture is stirred for 5 hours and then stored at 40° for 16 hours. The chilled reaction solution is diluted with water (300 mL) and acetone is evaporated under reduced pressure. The aqueous slurry remaining is extracted with EtOAc (2×300 mL) and the combined organic phases are washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL), dried over MgSO4, filtered and concentrated. The residue is purified by flash chromatography (1:1 EtOAc/CH2Cl2) to afford 3-hydroxy-androst-5,15(16)-dien-17-one (C3-alcohol).

Workup

  1. customThe 0° reaction mixture
  2. waitstored at 40° for 16 hours
  3. customThe chilled reaction solution
  4. customis evaporated under reduced pressure
  5. extractionThe aqueous slurry remaining is extracted with EtOAc (2×300 mL)
  6. washthe combined organic phases are washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified by flash chromatography (1:1 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-66a3a5f7968249e6a103502018a190fd
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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