Pyridine → HCID 13020861, compound

HRID 279851Notes

Reaction equation

HRID 279851 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([CH2:12][C:13](=[O:22])[CH2:14][C@@H:15]1[CH3:21])[CH2:10][CH2:9]3.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.N1[CH:39]=[CH:38]C=CC=1>C1(C)C=CC=CC=1.C(O)CO.C(OCC)C>[CH2:39]1[CH2:38][O:30][C:13]2([CH2:14][C@H:15]([CH3:21])[C@@:16]3([CH3:17])[C@@H:11]([CH2:10][CH2:9][C@@H:8]4[C@@H:18]3[CH2:19][CH2:20][C@@:3]3([CH3:4])[C@H:5]4[CH2:6][CH2:7][C@@H:2]3[OH:1])[CH2:12]2)[O:22]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 15020Mesterolone

Product 1

HCID 13020861HCID 13020861, compound

Reagents, catalysts & solvents 3

HCID 174Ethylene GlycolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 30 g of 17β-hydroxy-1α-methyl-5α-androstan-3-one in 300 ml of toluene and 90 ml of ethylene glycol is combined with 900 mg of p-toluenesulfonic acid and stirred for 6 hours with gradual removal by distillation. After cooling, the reaction solution is mixed with 3 ml of pyridine, diluted with diethyl ether, and washed with water. After evaporation, 35 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol is obtained.

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. customAfter evaporation

Sources & evidence

ORD record
ord-eacfafcf260d4a119a35e846722fbf39
Source dataset
uspto-grants-1986_05
Patent number
US04587235

Reaction notes

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