Dehydroepiandrosterone → 3Betabenzyloxycarbonyloxy-5androsten-17-one

HRID 1956134Notes

Reaction equation

HRID 1956134 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
  3. dissolutionis 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-ee3eb7b995c54d0db28bcff8bc09ad22
Source dataset
uspto-grants-1998_07
Patent number
US05780460

Reaction notes

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