Methanol → HCID 89975735, compound

HRID 716122Notes

Reaction equation

HRID 716122 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1.[F:12][C@@H:13]1[CH:17]([O:18][CH3:19])[O:16][C@H:15]([CH2:20][OH:21])[C@H:14]1[OH:22].CO>CN(C)C=O>[F:12][C@H:13]1[C@H:14]([O:22][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([CH3:3])=[CH:5][CH:6]=2)[C@@H:15]([CH2:20][O:21][CH2:3][C:4]2[CH:11]=[CH:10][C:7]([CH3:8])=[CH:6][CH:5]=2)[O:16][CH:17]1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 7721p-Xylyl bromideHCID 24758Sodium hydrideHCID 20768265HCID 20768265, compound

Product 1

HCID 89975735HCID 89975735, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a nitrogen atmosphere, 0.44 g of sodium hydride and 2.03 g of 4-methylbenzyl bromide were added to a solution of 0.70 g of (2R,3R,4S)-4-fluoro-2-(hydroxymethyl)-5-methoxyoxolan-3-ol in 7.0 mL of N,N-dimethylformamide under cooling on ice, and the obtained mixture was then stirred at room temperature for 2 hours. Thereafter, 2.5 mL of methanol was added to the reaction mixture to terminate the reaction, and ethyl acetate and hexane were then added thereto. The reaction mixture was successively washed with water and a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 60/40), so as to obtain 1.33 g of (3S,4R,5R)-3-fluoro-2-methoxy-4-((4-methylbenzyl)oxy)-5-(((4-methylbenzyl)oxy)methyl)oxolane in the form of a colorless oily product.

Workup

  1. temperatureunder cooling on ice
  2. customto terminate
  3. customthe reaction, and ethyl acetate and hexane
  4. additionwere then added
  5. washThe reaction mixture was successively washed with water
  6. dry with materiala saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate
  7. distillationAfter that, the solvent was distilled away under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 60/40)

Sources & evidence

ORD record
ord-a31a349ebe344ee483d4021bdde3b8b2
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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