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

HRID 918059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918059
[Cl:1][CH2:2][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>O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[Cl:1][CH2:2][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

Komponenten

3

Edukt 1

HCID 2279148521-(3'-Chloropropoxy)-5alpha-pregnane-3,11,20-trione

Produkt 1

HCID 2279148421-(3'-Chloropropoxy)-3alpha-hydroxy-5alpha-pregnane-11,20-dioneAusbeute 48,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

The less polar residue, crude 21-(3'-chloropropoxy)-5α-pregnane-3,11,20-trione (1.1 g.) was treated with `stock` chloroiridic acid solution. The mixture was then refluxed for 24 hours, cooled and partitioned between water and ether. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was subjected to preparative t.l.c. EtOAc/petrol 1:1 to give title compound (0.54 g.) as a white foam, [α]D + 73° (c 1.3).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-597d44c9671e4854969dedbacdbf017a
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03969345

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