Cholesterol → Pregnanolone

HRID 2254017

Reaktionsgleichung

Reaktionsgleichung von HRID 2254017
C(O)(=O)CCC(O[C@H]1CC[C@@:29]2([CH3:32])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:28]2CC[C@@]2(C)[C@H]3CC[C@@H]2[C@H](C)CCCC(C)C)[CH2:8]1)=O.I[C:37]#N.C(O)[C:40](N)([CH2:43]O)[CH2:41][OH:42].CC(CCC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H:70](CC2)[C@:68]2(C)[C:62]([CH2:63][C@H:64]([CH2:66][CH2:67]2)[OH:65])=[CH:61][CH2:60]3)CC1)C)C>O>[CH3:37][C:41]([C@@H:40]1[C@@:29]2([CH3:32])[CH2:28][CH2:12][C@@H:11]3[C@@:68]4([CH3:70])[CH2:67][CH2:66][C@@H:64]([OH:65])[CH2:63][C@H:62]4[CH2:61][CH2:60][C@H:10]3[C@@H:9]2[CH2:8][CH2:43]1)=[O:42]

Komponenten

6

Edukt 4

HCID 5997CholesterolHCID 6503Tris(hydroxymethyl)aminomethane2×HCID 10478Cyanogen iodideHCID 65082Cholesteryl hemisuccinate

Produkt 1

HCID 31402Pregnanolone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The cholesterol hemisuccinate Tris salt had been prepared as follows Cholesterol hydrogen succinate (50.3 g, 0.11 moles) from ICN, Cleveland, Ohio, was dissolved in 1.5 liters of diethyl either. Tris base (12.1 g, 0.1 moles) from Fisher, Fairlawn, N.J., was dissolved in 30 ml of water. The Tris solution was then added to the cholesterol solution, and the resulting solution was rotoevaporated to a milky wet residue. The milky residue was freeze dried for 12 hours, after which the cholesterol hemisuccinate Tris salt product was recrystallized three times from about 5-liter volumes of boiling ethyl acetate.

Aufarbeitung

  1. dissolutionwas dissolved in 1.5 liters of diethyl either
  2. customdried for 12 hours
  3. customafter which the cholesterol hemisuccinate Tris salt product was recrystallized three times from about 5-liter volumes of boiling ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-30e186780f784fa4a9d3d367033dac61
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05234634

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