Ethanol → HCID 69904879, compound

HRID 1837122Notes

Reaction equation

HRID 1837122 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 699057232beta-Isopropoxy-3alpha-hydroxy-5alpha-androstan-17-one

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 (4×45 mL). 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 (4×45 mL)
  5. dry with materialIt was then dried over Na2SO4 and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-f84cd5a102654db4a56fd0edd34fb564
Source dataset
uspto-grants-2004_08
Patent number
US06780853B1

Reaction notes

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