Dehydroepiandrosterone → 3Betabenzyloxycarbonyloxy-5androsten-17-one

HRID 399728

Reaction equation

HRID 399728 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-9629cd14e1e248efaddf13aea36ee1bd
Source dataset
uspto-grants-1998_10
Patent number
US05824671

Linked notes

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