Ethanol → HCID 69904879, compound

HRID 582518Notes

Reaction equation

HRID 582518 reaction equation
[CH:1]([O:4][C@H:5]1[CH2:22][C@@:21]2([CH3:23])[C@@H:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=O)[CH2:7][C@@H:6]1[OH:25])([CH3:3])[CH3:2].[C:26]1([CH3:37])[CH:31]=[CH:30][C:29]([S:32]([NH:35][NH2:36])(=[O:34])=[O:33])=[CH:28][CH:27]=1.C(O)C>C(Cl)Cl>[S:32]([NH:35][N:36]=[C:15]1[CH2:14][CH2:13][C@H:12]2[C@H:11]3[C@H:20]([CH2:19][CH2:18][C@:16]12[CH3:17])[C@:21]1([CH3:23])[C@H:8]([CH2:7][C@H:6]([OH:25])[C@@H:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH2:22]1)[CH2:9][CH2:10]3)([C:29]1[CH:28]=[CH:27][C:26]([CH3:37])=[CH:31][CH:30]=1)(=[O:33])=[O:34]

Participants

5

Reactant 3

HCID 702EthanolHCID 15303P-ToluenesulfonylhydrazideHCID 69905723HCID 69905723, compound

Product 1

HCID 69904879HCID 69904879, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2β-isopropoxy-3α-hydroxy-5α-androstan-17-one (700 mg, 2.0 mmol) and p-toluenesulfonhydrazide (450 mg, 2.4 mmol) was added ethanol (2 mL) and the mixture obtained was heated to reflux for 12 h. Then the reaction mixture was dissolved in CH2Cl2 (150 mL) and washed with water (4×45mL). It was then dried over Na2SO4 and removal of the solvent in vacuo resulted in the crude 2β-isopropoxy-3α-hydroxy-5α-androstan-17-one tosylhydrazone (1.113 g), which was used without further purification for the next step.

Workup

  1. customthe mixture obtained
  2. temperaturewas heated
  3. temperatureto reflux for 12 h
  4. washwashed with water (4×45mL)
  5. dry with materialIt was then dried over Na2SO4 and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-2c52c56342154da09534a2a8f926c8d6
Source dataset
uspto-grants-1999_07
Patent number
US05925630

Reaction notes

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