Hydrochloric Acid → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3alpha-ol

HRID 1196358Notes

Reaction equation

HRID 1196358 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:7][O:6][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17](=[CH:18][C:19](=[O:30])[C@@H:20]5[O:29][C@@H:21]53)[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:4][CH2:3]1.[BH4-].[Na+].Cl>C(O)C.O>[CH3:31][C:2]1([CH3:1])[CH2:3][O:4][CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17](=[CH:18][C@H:19]([OH:30])[C@@H:20]5[O:29][C@@H:21]53)[CH:16]=[CH:15]4)[CH2:12][CH2:11]2)[CH3:9])[O:6][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

Product 1

HCID 8674582720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3alpha-olYield 81.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 200 ml of ethanol was dissolved 13.0 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one, followed by addition of 1.0 g of sodium borohydride under ice-cooling. The mixture was stirred at room temperature for 2 hours. The resulting reaction mixture was neutralized with diluted hydrochloric acid under ice-cooling, diluted with water and extracted with methylene chloride. The extract was washed with aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure to recover 12.1 g of a crude product. Purification of this crude product by silica gel chromatography gave 10.6 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3α-ol (yield: 81%) having the following physical properties.

Workup

  1. temperaturecooling
  2. customThe resulting reaction mixture
  3. temperaturecooling
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customto recover 12.1 g of a crude product
  9. customPurification of this crude product by silica gel chromatography

Sources & evidence

ORD record
ord-e5c7b60009cc46d288afeae82bc01626
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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