تفاعل #413673

ord-8da3ab01dd7c4cc79ba58dc25de1dee6

معادلة التفاعل

CC(=O)[C@H]1[C@H](C)C[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C
3α-hydroxy-16α-methyl-5α-pregnan-20-one
ClC(Cl)(Cl)Cl
carbon tetrachloride
[Ca+2].[O-2]
calcium oxide
II
iodine
→
C[C@@H]1C[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1C(=O)CI
title compound
C[C@@H]1C[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)[C@H]1C(=O)CI
3α-Hydroxy-21-iodo-16α-methyl-5α-pregnan-20-one

المتفاعلات

CC(=O)[C@H]1[C@H](C)C[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C
3α-hydroxy-16α-methyl-5α-pregnan-20-one
ClC(Cl)(Cl)Cl
carbon tetrachloride
[Ca+2].[O-2]
calcium oxide
—
steroid
II
iodine

الكواشف

لا شيء

المذيبات

CO
methanol
[Ca+2].[Cl-].[Cl-]
calcium chloride
C1CCOC1
THF
[Ca+2].[Cl-].[Cl-]
calcium chloride

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGThe mixture is stirred an additional 2 hr at 30°
  2. 2
    ترشيحfiltered through a pad of filter aid
  3. 3
    تركيزthe filtrate concentrated under reduced pressure to an oil
  4. 4
    workup.DISSOLUTIONThe oil is dissolved in methylene chloride
  5. 5
    أخرىflash chromatographed over silica gel (100 g)
  6. 6
    غسيلeluting with methylene chloride/ethyl acetate (4/1)
  7. 7
    تركيزconcentrated
  8. 8
    أخرىthe residue triturated with ether

الإجراء التجريبي

A mixture of 3α-hydroxy-16α-methyl-5α-pregnan-20-one (21 g) methanol (80 ml), carbon tetrachloride (40 ml), THF (120 ml), calcium oxide (25 g) and calcium chloride in methanol (10%, 3 ml) is stirred at 25°-30°. A solution of iodine (20 g) in calcium chloride (10%, 70 ml) is added to the steroid mixture over 1 hr. The mixture is stirred an additional 2 hr at 30°, filtered through a pad of filter aid, and the filtrate concentrated under reduced pressure to an oil. The oil is dissolved in methylene chloride and flash chromatographed over silica gel (100 g) eluting with methylene chloride/ethyl acetate (4/1). The appropriate fractions are pooled, concentrated and the residue triturated with ether to give the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05268477uspto-grants-1993_12