Cholesterol → Pregnanolone

HRID 2248543Notes

Reaction equation

HRID 2248543 reaction equation
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>C(OCC)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]

Participants

7

Reactant 4

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

Product 1

HCID 31402Pregnanolone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

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 ether. 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.

Workup

  1. customdried for 12 hours
  2. customafter which the cholesterol hemisuccinate Tris salt product was recrystallized three times from about 5-liter volumes of boiling ethyl acetate

Sources & evidence

ORD record
ord-06bc4217137f47edac0d9fdbd5fde886
Source dataset
uspto-grants-1991_08
Patent number
US05041278

Reaction notes

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