Hydrochloric Acid → HCID 9818439, compound

HRID 2255161Notes

Reaction equation

HRID 2255161 reaction equation
[BH4-].[Li+].[CH2:3]([O:10][C:11]1[C:12]([CH2:24][CH:25]([CH3:27])[CH3:26])=[N+:13]([O-:23])[C:14]([O:21][CH3:22])=[C:15]([C:17](OC)=[O:18])[N:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C(OCC)C.O>[CH2:3]([O:10][C:11]1[C:12]([CH2:24][CH:25]([CH3:27])[CH3:26])=[N+:13]([O-:23])[C:14]([O:21][CH3:22])=[C:15]([CH2:17][OH:18])[N:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 10970054HCID 10970054, compound

Product 1

HCID 9818439HCID 9818439, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

2.4 Milligrams of lithium borohydride was added to 1 ml of a solution of 12.5 mg of 3-benzyloxy-2-isobutyl-6-methoxy-5-methoxycarbonylpyrazine 1-oxide dissolved in anhydrous diethyl ether. The mixture was refluxed for 6 hours in an argon gas stream with stirring, then 0.2 ml of 1N hydrochloric acid was added to the reaction mixture with ice cooling, and the mixture was diluted with water. The reaction mixture was extracted with ethyl acetate and the extract was washed with an aqueous solution saturated with NaCl solution and dried over magnesium sulfate, and the solvent was removed by evaporation. The residue was purified by a thin layer chromatography (developing solvent: dichloromethane/methanol=40/1) to obtain 3.5 mg of 3-benzyloxy-5-hydroxymethyl-6-methoxy-2-isobutylpyrazine 1-oxide (Compound B-24) as colorless needle-like crystals having a melting point of 68.0°-69.2° C.

Workup

  1. temperatureThe mixture was refluxed for 6 hours in an argon gas stream
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with an aqueous solution saturated with NaCl solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by a thin layer chromatography (developing solvent: dichloromethane/methanol=40/1)

Sources & evidence

ORD record
ord-95b59c1ecaf04b44b9718ef17da29fdb
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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