Hydride → HCID 69885745, compound

HRID 1059401Notes

Reaction equation

HRID 1059401 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14]/[CH:15]=[CH:16]/[C:17](OCC)=[O:18])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:22]=[CH:23][CH:24]=[N:25][C:5]1=2.[H-]>ClCCl.C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH2:14][CH:15]=[CH:16][CH2:17][OH:18])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:22]=[CH:23][CH:24]=[N:25][C:5]1=2

Participants

5

Reactant 2

HCID 166653HydrideHCID 18670352HCID 18670352, compound

Product 1

HCID 69885745HCID 69885745, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2.9 g of ethyl(E)-3-[10-(methoxymethyl)-10H-pyrazino-[2,3-b][1,4]benzothiazin-8-ylmethyl]propenoate was dissolved in 20 ml of dry dichloromethane in a nitrogen atmosphere and ice-cooled. The reaction mixture was stirred and 5.8 ml of a 1.5 M solution of isobutylalminum hydride in toluene was dropped thereinto. After stirring for 2 hours, the reaction mixture was poured into ice-ethyl acetate and stirred for 30 minutes. The insoluble matters were removed by filtering the reaction mixture thorough celite. Then the organic layer was extracted, washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 1.4 g of 3-[10-(methoxymethyl)-10H-pyrazino-[2,3-b][1,4]benzothiazin-8-ylmethyl]-2-propen-1-ol as a pale yellow oily substance. The obtained compound was dissolved in 10 ml of hexachloroacetone and 1.34 g of triphenylphosphine was added in several portions thereto under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was distributed into an aqueous solution of sodium bicarbonate and diethyl ether and extracted with ether. After drying over anhydrous sodium sulfate and distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 230 mg of the title compound as yellow crystals.

Workup

  1. temperaturecooled
  2. stirringAfter stirring for 2 hours
  3. stirringstirred for 30 minutes
  4. customThe insoluble matters were removed
  5. filtrationby filtering the reaction mixture thorough celite
  6. extractionThen the organic layer was extracted
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationAfter distilling off the solvent under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-fd7ef6393a3c429c8e69a36b8692bdca
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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