Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 4-(tert-Butyldimethylsilyloxy)cyclohexanone | HCID 10609430 | — |
| Reactant | HCID 178418311 | HCID 178418311 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Product | HCID 178455070 | HCID 178455070 | 20.8% |
Reaction Steps
To a solution (30 mL) of 1H-1,2,4-triazol-3-amine (3 g) and 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanone (10 g) in acetic acid was added sodium cyanoborohydride (9.3 g), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the solvent was evaporated under reduced pressure. The obtained residue was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with a mixed solvent of ethyl acetate and isopropyl alcohol (3:1). The obtained extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (2.2 g, 20%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09115136B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-318f3816bd324739ad380af490178a5f |
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| Source note | uspto-grants-2015_08 |
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