Hydrogen Peroxide → 21,21-Dimethoxy-20-methylpregn-6-ene-1alpha,3beta,5a-triol

HRID 1196361Notes

Reaction equation

HRID 1196361 reaction equation
O1[CH:24]2[C:25](=[O:26])[C@:2]31[O:29][C@:3]13[C@:22]([CH3:27])([CH2:23]2)[C@@H:21]2[C@H:6]([C@H:7]3[C@:18]([CH3:28])([CH2:19][CH2:20]2)[C@@H:10]([CH:11]([CH3:17])[CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH2:9][CH2:8]3)[CH:5]=[CH:4]1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH2:44].OO>O1CCCC1>[CH3:16][O:15][CH:12]([O:13][CH3:14])[CH:11]([CH3:17])[C@@H:10]1[C@:18]2([CH3:28])[C@H:7]([C@H:6]3[C@H:21]([CH2:20][CH2:19]2)[C@:22]2([CH3:27])[C@:3]([OH:29])([CH2:2][C@@H:25]([OH:26])[CH2:24][C@@H:23]2[OH:44])[CH:4]=[CH:5]3)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3611392Lithium tri-s-butylborohydrideHCID 867458304alpha,5alpha-Diepoxy-21,21-dimethoxy-20-methylpregn-6-en-3-one

Product 1

HCID 5708541221,21-Dimethoxy-20-methylpregn-6-ene-1alpha,3beta,5a-triol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of tetrahydrofuran was dissolved 8.5 g of the 1α,2α;4α,5α-diepoxy-21,21-dimethoxy-20-methylpregn-6-en-3-one obtained in Example 76, followed by dropwise addition of 100 ml of a 1.0M solution of lithium tri-sec-butylborohydride in tetrahydrofuran under ice-cooling. After completion of dropwise addition, the mixture was stirred at room temperature for 2 hours. The excess reducing agent was decomposed with water and the residual alkylborane was decomposed with alkaline hydrogen peroxide, followed by extraction with ethyl acetate. The extracts were pooled, washed with aqueous sodium chloride solution, and dried over sodium sulfate, followed by concentration under reduced pressure. Recrystallization of the concentrate from ethyl acetate gave 2.90 g of 21,21-dimethoxy-20-methylpregn-6-ene-1α,3β,5a-triol showing the following physical properties.

Workup

  1. temperaturecooling
  2. additionAfter completion of dropwise addition
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashed with aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customRecrystallization of the
  8. concentrationconcentrate from ethyl acetate

Sources & evidence

ORD record
ord-f6beaba0278f465889562b1ebbff0cbc
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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