Methanol → HCID 89975644, compound

HRID 1508621Notes

Reaction equation

HRID 1508621 reaction equation
[H-].[Na+].[Cl: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]1O.[CH3:23][OH:24]>CN(C)C=O>[Cl:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:23][O:24][C@H:14]2[C@H:13]([F:12])[CH:17]([O:18][CH3:19])[O:16][C@@H:15]2[CH2:20][O:21][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([Cl:3])=[CH:5][CH:6]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 20768265HCID 20768265, compound

Product 1

HCID 89975644HCID 89975644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a nitrogen atmosphere, 0.97 g of sodium hydride and 4.66 g of 4-chlorobenzyl bromide were added to a solution of 1.35 g of (2R,3R,4S)-4-fluoro-2-(hydroxymethyl)-5-methoxyoxolan-3-ol in 13 mL of N,N-dimethylformamide under cooling on ice, and the obtained mixture was then stirred at room temperature for 1 hour. Thereafter, 5 mL of methanol was added to the reaction mixture to terminate the reaction, and ethyl acetate and hexane were then added to the mixture. The thus obtained mixture was successively washed with water, a saturated sodium hydrogen carbonate aqueous solution 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=100/0 to 60/40), so as to obtain 3.32 g of (2R,3R,4S)-3-((4-chlorobenzyl)oxy)-2-(((4-chlorobenzyl)oxy)methyl)-4-fluoro-5-methoxyoxolane 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 to the mixture
  5. washThe thus obtained mixture was successively washed with water
  6. dry with materiala saturated sodium hydrogen carbonate aqueous solution and a 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=100/0 to 60/40)

Sources & evidence

ORD record
ord-b59c9e9f2f79405cba127106d2fcbced
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

Loading…