Hydrochloric Acid → HCID 53776670, compound

HRID 1275692Notes

Reaction equation

HRID 1275692 reaction equation
[OH:1][CH2:2][C:3]1[C@H:7]2[C@H:8]([O:16][CH3:17])[O:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C@H:6]2[CH2:5][CH:4]=1.C(N(CC)CC)C.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].Cl>CN(C)C=O>[Si:25]([O:1][CH2:2][C:3]1[C@H:7]2[C@H:8]([O:16][CH3:17])[O:9][CH:10]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C@H:6]2[CH2:5][CH:4]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 13988265HCID 13988265, compound

Product 1

HCID 53776670HCID 53776670, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3 g (12.5 mmol) of methyl (1R,4aS,7aS)-7-hydroxymethyl-1-methoxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran4-carboxylate was dissoved in 50 ml of dimethylformamide and 1.9 ml (13.8 mmol) of triethylamine was added thereto under nitrogen atmosphere. The reaction solution was stirred for one hour and then 2.07 g (13.8 mmol) of t-butyldimethylsilylchloride dissolved in 10 ml of dimethylformamide was added dropwise thereto. After stirring for 3 hours, 1N-aqueous hydrochloric acid solution was added in order to stop the reaction. Organic layer was extracted by the addition of diethylether and then it was washed with saturated aqueous sodium bicarbonate solution and saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain 4.16 g (Yield 94%) of methyl (1R,4aS,7aS)-7-(t-butyldimethylsilyloxymethyl)-1 -methoxy-1,4a,5,7a-tetrahydrocyclo penta[c]pyran-4-carboxylate as a colorless oil.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for 3 hours
  3. customthe reaction
  4. extractionOrganic layer was extracted by the addition of diethylether
  5. washit was washed with saturated aqueous sodium bicarbonate solution and saturated saline solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b478e8d9611d4abf98f7ee01b351c7a6
Source dataset
uspto-grants-2000_12
Patent number
US06162826

Reaction notes

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