Reacción #2079

ord-1079585e7a194106a0429ed7ca89727f

Ecuación de reacción

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
O=C(Cl)OCc1ccccc1
benzylchloroformate
→
C[C@]12CC[C@H](OC(=O)OCc3ccccc3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3β-benzyloxycarbonyloxy-5-androsten-17-one

Reactantes

C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
dehydroepiandrosterone
O=C(Cl)OCc1ccccc1
benzylchloroformate

Reactivos

Ninguno

Disolventes

ClCCl
methylene chloride

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadothe mixture is washed with water
  2. 2
    Otroevaporated to dryness
  3. 3
    workup.DISSOLUTIONThe residue is then dissolved in acetone
  4. 4
    Otroprecipitated in iced water
  5. 5
    workup.WAITAfter 16 h
  6. 6
    Filtracióncrystals are filtered
  7. 7
    Otrodried in vacuo

Procedimiento

To a stirred solution of dehydroepiandrosterone (2.88 % 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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05728688uspto-grants-1998_03