Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 10970054 | HCID 10970054 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 9818439 | HCID 9818439 | 30.5% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05238938 |
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| Source dataset | uspto-grants-1993_08 |
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| ORD ID | ord-95b59c1ecaf04b44b9718ef17da29fdb |
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| Source note | uspto-grants-1993_08 |
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