Hydrogen Peroxide → HCID 70628079, compound

HRID 1834953Notes

Reaction equation

HRID 1834953 reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[C:15]([OH:18])(=[O:17])[CH3:16].O[CH2:20][C@@:21]12[C@@H:38]3[C@H:29]([C@H:30]4[C@@:34]([CH2:36][CH2:37]3)([CH3:35])[C:33](=[O:39])[CH2:32][CH2:31]4)[CH2:28][CH2:27][C:26]1=[CH:25][C:24](=[O:40])[CH2:23][CH2:22]2.[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:15]([O:18][CH2:20][C@@:21]12[C@@H:38]3[C@H:29]([C@H:30]4[C@@:34]([CH2:36][CH2:37]3)([CH3:35])[C@@H:33]([OH:39])[CH2:32][CH2:31]4)[CH2:28][CH2:27][C:26]1=[CH:25][C@H:24]([OH:40])[CH2:23][CH2:22]2)(=[O:17])[CH3:16]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 86734750HCID 86734750, compound

Product 1

HCID 70628079HCID 70628079, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1 M solution of lithium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled in a dry iceacetone bath to about -78° C. and 19-hydroxyandrost-4-ene-3,17-dione acetate in tetrahydrofuran is slowly added. The reaction mixture is stirred for a period of 2 hours at this temperature, warmed to 0° C., and stirring continued for an additional two hours. The reaction mixture is decomposed by the addition of 3 N sodium hydroxide followed by the addition of a 30% hydrogen peroxide solution. Care is taken that the solution temperature remains below 10° C. during decomposition. Solid potassium carbonate is added and the tetrahydrofuran decanted. The solid residue is washed with tetrahydrofuran and the combined solutions are dried over sodium sulfate, filtered and evaporated. The residue which remains is crystallized from acetone to yield 4-androstene-3α,17β,19-triol 19-acetate.

Workup

  1. stirringstirring
  2. waitcontinued for an additional two hours
  3. customremains below 10° C. during decomposition
  4. customthe tetrahydrofuran decanted
  5. washThe solid residue is washed with tetrahydrofuran
  6. dry with materialthe combined solutions are dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue which remains is crystallized from acetone

Sources & evidence

ORD record
ord-ed2726e265874f7e9e8f1699cf5bfe43
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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