Dehydroepiandrosterone → 3Betabenzyloxycarbonyloxy-5androsten-17-one

HRID 362768

Reaction equation

HRID 362768 reaction equation
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[CH2:22]([O:29][C:30](Cl)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30]([O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 5881DehydroepiandrosteroneHCID 10387Benzyl chloroformate

Product 1

HCID 542344703Betabenzyloxycarbonyloxy-5androsten-17-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of dehydroepiandrosterone (2.88 g, 10 mmol) in methylene chloride (100 mL) is added dropwise benzylchloroformate, over a period of 30 min following the known procedure (F. Reber and T. Reichstein, Helv. Chim. Acta, 28, 1164, 1945). After stirring for 3 h, the mixture is washed with water and evaporated to dryness. The residue is then dissolved in acetone and precipitated in iced water. After 16 h, crystals are filtered and dried in vacuo.

Workup

  1. washthe mixture is washed with water
  2. customevaporated to dryness
  3. dissolutionThe residue is then dissolved in acetone
  4. customprecipitated in iced water
  5. waitAfter 16 h
  6. filtrationcrystals are filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-acb57084100a4b42b0135c42120e0ae5
Source dataset
uspto-grants-1999_02
Patent number
US05872114

Linked notes

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