Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | HCID 58550808 | HCID 58550808 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 58551183 | HCID 58551183 | 71.5% |
Reaction Steps
To tert-butyl 3-(diethoxymethyl)-4-oxo-spiro[chromane-2,4′-piperidine]-1′-carboxylate (15.1 g, 35.9 mmol) and hydrazine (1.35 mL, 43.1 mmol) in EtOH (120 mL) was added hydrochloric acid (900 μL of 4.0 M in dioxanes, 3.6 mmol). The mixture was heated at 60° C. for 2 h before it was cooled and the solvent was evaporated. The residue was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexanes to give tert-butyl spiro[1H-chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carboxylate (8.76 g, 71%). ESI-MS m/z calc. 341.2. found 342.3 (M+1)+; Retention time: 1.69 minutes (3 min run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598164B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-b82ffbcf76174107830c6dbb4fc69602 |
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| Source note | uspto-grants-2013_12 |
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