Water → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1alpha,3beta-diol

HRID 1708760Notes

Reaction equation

HRID 1708760 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:37])[CH2:13][O:12][CH:11]([CH:14]([C@@H:16]2[C@:33]3([CH3:34])[C@H:19]([C:20]4[C@H:30]([CH2:31][CH2:32]3)[C@:28]3([CH3:29])[C:23]([CH2:24][C@@H:25]([OH:36])[C@@H:26]5[O:35][C@@H:27]53)=[CH:22][CH:21]=4)[CH2:18][CH2:17]2)[CH3:15])[O:10][CH2:9]1.O.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH3:37][C:8]1([CH3:7])[CH2:9][O:10][CH:11]([CH:14]([C@@H:16]2[C@:33]3([CH3:34])[C@H:19]([C:20]4[C@H:30]([CH2:31][CH2:32]3)[C@:28]3([CH3:29])[C:23]([CH2:24][C@@H:25]([OH:36])[CH2:26][C@@H:27]3[OH:35])=[CH:22][CH:21]=4)[CH2:18][CH2:17]2)[CH3:15])[O:12][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 21226206Ethyl acetate hexaneHCID 21226445Aluminium lithium hydride2×HCID 2284392220-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-5,7-dien-3beta-ol

Product 1

HCID 6785294520-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1alpha,3beta-diolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 4 mg (0.1 mmole) of lithium aluminum hydride in 4 ml of dry tetrahydrofuran was added a solution of 3.8 mg (0. 00887 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-5,7-dien-3β-ol in 2 ml of dry tetrahydrofuran at a temperature of 60° C. and the mixture was stirred at 60° C. for 30 minutes. To the reaction mixture was added water to decompose the excess lithium aluminum hydride and the tetrahydrofuran was distilled off under reduced pressure at a temperature not exceeding 60° C. To the residue was added cold 1N-hydrochloric acid and the mixture was extracted with chloroform. The extract was washed with aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:ethyl acetate-hexane=1:5, v/v) to give 3 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1α,3β-diol (yield: ca. 80%).

Workup

  1. distillationthe tetrahydrofuran was distilled off under reduced pressure at a temperature not
  2. customexceeding 60° C
  3. additionTo the residue was added cold 1N-hydrochloric acid
  4. extractionthe mixture was extracted with chloroform
  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. customthe residue was purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-872bdcfde5bf43e0abc361e08de94503
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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