21-(2'-Cyanoethoxy)-5alpha-pregnane-3,11,20-trione → 21-(2'-Cyanoethoxy)-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 918058노트

반응식

HRID 918058 반응식
[C:1]([CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:29])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C:23](=[O:27])[CH2:24]2)[C@:20]2([CH3:21])[C@H:15]([CH2:16][C:17](=[O:28])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)#[N:2]>O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[C:1]([CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:29])[C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@H:22]([C:23](=[O:27])[CH2:24]2)[C@:20]2([CH3:21])[C@H:15]([CH2:16][C@H:17]([OH:28])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)#[N:2]

참가 물질

3

반응물 1

HCID 2279148021-(2'-Cyanoethoxy)-5alpha-pregnane-3,11,20-trione

생성물 1

HCID 2279147921-(2'-Cyanoethoxy)-3alpha-hydroxy-5alpha-pregnane-11,20-dione수율 0.2%

시약·촉매·용매 1

HCID 16211483Tetrachloroiridium--hydrogen chloride--water (1/2/1)촉매

실험 절차

The product, crude 21-(2'-cyanoethoxy)-5α-pregnane-3,11,20-trione (0;80 g.) was treated with chloroiridic acid solution (24 ml.). The mixture was refluxed for 24 hours cooled and partitioned between water and ether. The organic layer was washed with saturated aqueous sodium bicarbonate, water, dried (Na2SO4) and evaporated. The residue was subjected to preparative t.l.c. EtOAc, petrol (1:1) to give title compound (0.2 g.) as a white foam, [α]D + 85° (c 1.1).

후처리

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperaturecooled
  3. custompartitioned between water and ether
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water
  5. dry with materialdried (Na2SO4)
  6. customevaporated

출처 및 근거

ORD 기록
ord-4b63a3f388e649d4be7738fa6366b288
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03969345

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