Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | Sodium Hypochlorite | HCID 23665760 | — |
| Reactant | HCID 117988010 | HCID 117988010 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 103563890 | HCID 103563890 | 51.7% |
Reaction Steps
To a solution of tert-butyl 2-(2,2-dimethylcyclopentylidene)hydrazinecarboxylate (4.6 g) and acetic acid (9.4 g) in THF (80 mL) was added sodium cyanoborohydride (5.1 g) at room temperature. The reaction mixture was stirred at 85° C. for 10 hr, aqueous sodium hypochlorite solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (2.4 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09371320B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-f10e0a5b0c7b48eab27865d75326cda1 |
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| Source note | uspto-grants-2016_06 |
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