Triethylamine → 20,20-Ethylenedioxy-3alpha-hydroxy-2alpha-methyl-5alpha-pregnane-11-one

HRID 1606488노트

반응식

HRID 1606488 반응식
P(OC)(OC)OC.C(N(CC)CC)C.[CH2:15]1[CH2:42][O:41][C:17]([C@@H:19]2[C@:36]3([CH3:37])[C@H:22]([C@H:23]4[C@H:33]([C:34](=[O:38])[CH2:35]3)[C@:31]3([CH3:32])[C@H:26]([CH2:27][C:28](=[O:40])[C@@H:29]([CH3:39])[CH2:30]3)[CH2:25][CH2:24]4)[CH2:21][CH2:20]2)([CH3:18])[O:16]1>C(O)(C)C.O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[CH2:42]1[CH2:15][O:16][C:17]([C@@H:19]2[C@:36]3([CH3:37])[C@H:22]([C@H:23]4[C@H:33]([C:34](=[O:38])[CH2:35]3)[C@:31]3([CH3:32])[C@H:26]([CH2:27][C@H:28]([OH:40])[C@H:29]([CH3:39])[CH2:30]3)[CH2:25][CH2:24]4)[CH2:21][CH2:20]2)([CH3:18])[O:41]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 8472Trimethyl phosphiteHCID 8673333220,20-Ethylenedioxy-2beta-methyl-5alpha-pregnane-3,11-dione

생성물 1

HCID 7058512720,20-Ethylenedioxy-3alpha-hydroxy-2alpha-methyl-5alpha-pregnane-11-one수율 63.3%

시약·촉매·용매 2

HCID 16211483Tetrachloroiridium--hydrogen chloride--water (1/2/1)촉매HCID 3776Isopropanol용매

실험 절차

A solution of chloroiridic acid (10 mg.) and trimethyl phosphite (1.5 ml.) in aqueous 90% isopropanol (20 ml.) was heated under reflux for 17 hours. The solution was then neutralised with triethylamine, 20,20-ethylenedioxy-2β-methyl-5α-pregnane-3,11-dione (0.66 g.) was added, and the mixture was heated under reflux for 48 hr. The reaction mixture was cooled and partitioned between methylene chloride and water. The organic layer was dried (MgSO4) and evaporated in vacuo. The residue (0.69 g.) was purified by preparative layer chromatography and crystallised from methyl acetate/petroleum ether (b.p. 60°-80°) to give 20,20-ethylenedioxy-3α-hydroxy-2α-methyl-5α-pregnan-11-one (0.42 g.), m.p. 167°-168°, [α]D + 68°.

후처리

  1. temperatureunder reflux for 17 hours
  2. additionwas added
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 48 hr
  5. temperatureThe reaction mixture was cooled
  6. custompartitioned between methylene chloride and water
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customevaporated in vacuo
  9. customThe residue (0.69 g.) was purified by preparative layer chromatography
  10. customcrystallised from methyl acetate/petroleum ether (b.p. 60°-80°)

출처 및 근거

ORD 기록
ord-390ef995a30c4c33a80453265931943e
출처 데이터셋
uspto-grants-1976_04
특허 번호
US03953429

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