p-Toluenesulfonic acid → 3alpha-Hydroxy-2alpha-methyl-5alpha-pregnane-11,20-dione

HRID 1606489Notes

Reaction equation

HRID 1606489 reaction equation
C1CO[C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C:20](=[O:24])[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:26])[C@H:15]([CH3:25])[CH2:16]3)[CH2:11][CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[OH:26][C@@H:14]1[C@H:15]([CH3:25])[CH2:16][C@@:17]2([CH3:18])[C@@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[C:20](=[O:24])[CH2:21][C@@:22]2([CH3:23])[C@H:8]3[CH2:7][CH2:6][C@@H:5]2[C:3](=[O:2])[CH3:4])[CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 7058512720,20-Ethylenedioxy-3alpha-hydroxy-2alpha-methyl-5alpha-pregnane-11-one

Product 1

HCID 867333333alpha-Hydroxy-2alpha-methyl-5alpha-pregnane-11,20-dioneYield 51.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 20,20-ethylenedioxy-3α-hydroxy-2α-methyl-5α-pregnane-11-one (0.38 g.) and toluene-p-sulphonic acid (30 mg.) in acetone (20 ml.) was kept at room temperature for 11/2 hr. The reaction mixture was then evaporated to low bulk and an aqueous solution of sodium hydrogen carbonate was added. The precipitated solid (0.32 g.) was collected and purified by preparative t.l.c. and crystallised from methyl acetate/petrol (b.p. 60°-80°) to give the title compound (0.175 g.), m.p. 179°-180°, [α]D + 125°.

Workup

  1. customwas kept at room temperature for 11
  2. custom2 hr
  3. customThe reaction mixture was then evaporated to low bulk
  4. additionan aqueous solution of sodium hydrogen carbonate was added
  5. customThe precipitated solid (0.32 g.) was collected
  6. custompurified by preparative t.l.c
  7. customand crystallised from methyl acetate/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-b08d1a47a6da4a1994b865b402aa0a03
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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