تفاعل #2079

ord-1079585e7a194106a0429ed7ca89727f

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

ClCCl
methylene chloride

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    غسيلthe mixture is washed with water
  2. 2
    أخرىevaporated to dryness
  3. 3
    workup.DISSOLUTIONThe residue is then dissolved in acetone
  4. 4
    أخرىprecipitated in iced water
  5. 5
    workup.WAITAfter 16 h
  6. 6
    ترشيحcrystals are filtered
  7. 7
    أخرىdried in vacuo

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05728688uspto-grants-1998_03