Imidazole → HCID 123462581, compound

HRID 716156Notes

Reaction equation

HRID 716156 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[OH:12][CH2:13][C@@H:14]1[O:18][C:17]([CH3:20])([CH3:19])[O:16][C@@H:15]1[C@H:21]([OH:23])[CH3:22].N1C=CN=C1.C(OCC)(=O)C>CN(C)C=O.O>[CH3:20][C:17]1([CH3:19])[O:16][C@H:15]([C@H:21]([OH:23])[CH3:22])[C@H:14]([CH2:13][O:12][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[O:18]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 139400Triisopropylsilyl chlorideHCID 14037645HCID 14037645, compound

Product 1

HCID 123462581HCID 123462581, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4.46 mL of triisopropylsilyl chloride was added dropwise to a solution of 3.5 g of (1R)-1-((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl)ethan-1-ol and 1.63 g of imidazole in 50 mL of N,N-dimethylformamide in a nitrogen atmosphere at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 23 hours. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and it was washed with a saturated sodium chloride aqueous solution and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, so as to obtain 7.1 g of (1R)-1-((4R,5S)-2,2-dimethyl-5-(((tris(propan-2-yl)silyl)oxy)methyl)-1,3-dioxolane-4-yl)ethan-1-ol in the form of a colorless oily product.

Workup

  1. washit was washed with a saturated sodium chloride aqueous solution
  2. dry with materialwas then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-f4951c19a99347de8f36d1eeb586ef6d
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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