Hydrogen Peroxide → HCID 70614717, compound

HRID 1834994Notes

Reaction equation

HRID 1834994 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@H:26]1[CH2:25][C:24](=[O:40])[CH2:23][C@@H:22]2[CH3:41].[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@H:26]1[CH2:25][C@H:24]([OH:40])[CH2:23][C@@H:22]2[CH3:41])(=[O:17])[CH3:16]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 86735435HCID 86735435, compound

Product 1

HCID 70614717HCID 70614717, 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-hydroxy-1α-methyl-5α-androstane-3,17-dione acetate in tetrahydrofuran is slowly added. The reaction mixture is stirred for two 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 a 3 N sodium hydroxide solution 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 to the reaction mixture and the tetrahydrofuran decanted therefrom. The solid residue is washed with tetrahydrofuran and the combined solutions are dried over sodium sulfate, filtered and evaporated to dryness. The residue is crystallized from an acetone-hexane solution to yield 1α-methyl-5α-androstane-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 to dryness
  9. customThe residue is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-bd0ed585a1e943869560d27c24d8375a
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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