Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | 3-cyclopropyl-1H-pyrazol-5-amine | HCID 2758014 | — |
| Reactant | (1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid | HCID 21304923 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 69270826 | HCID 69270826 | — |
Reaction Steps
(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid (50 mg, 0.22 mmol, ee ˜90%) was mixed with toluene (1 ml), triethylamine (0.034 ml, 1.1 eq), 3-amino-5-cyclopropyl-1H-pyrazole (30 mg, 1.1 eq), DPPA (0.054 ml, 1.1 eq). The reaction mixture was then heated at stirring at 110° C. for 3 h. The reaction mixture was concentrated by rotary evaporation and two compounds were separated by column chromatography on silica (50 g, ethylacetate/hexane 1:3) to give 3 mg of the title product. The structure assignment was proved by 13C, gHMBC, gHMQC and NOESY NMR experiments.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07405310B2 |
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| Source dataset | uspto-grants-2008_07 |
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| ORD ID | ord-9cc00014978546bfbfeb6bd24b1d9092 |
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| Source note | uspto-grants-2008_07 |
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