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

HRID 1708794
Notes
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Reaction equation

HRID 1708794 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent
2×

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,5α-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-b34307aa6ce4464c8bc7092eb98fec28
Source dataset
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05359055

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes