Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | HCID 14437517 | HCID 14437517 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68500584 | HCID 68500584 | — |
Reaction Steps
A mixture of benzyl 3-oxo-1,4-diazepane-1-carboxylate (prepared according to Polish J. Chem. 1989, 63, 265-71), cyclopropylboronic acid (6 eq.), Et3N (10 eq.), pyridine (16 eq.) and Cu(OAc)2 (4 eq.) in dry THF (0.24 M) was heated for 10 min. to 140° C. in a microwave oven. After cooling to RT the mixture was filtered through celite, the solvents were removed under reduced pressure and the product was purified by chromatography on silica gel, eluenting with EtOAc/petroleum ether. The product was obtained as a white solid. 1H-NMR (300 MHz, CDCl3) δ: 7.45-7.22 (5H, m), 5.15 (2H, s), 4.22-4.07 (2H, m), 3.70-3.37 (4H, m), 2.75-2.60 (1H, m), 1.90-1.65 (2H, m), 0.85-0.72 (2H, m), 0.60-0.41 (2H, m). MS (ES) C16H20N2O3 requires: 288, found: 289 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08268827B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-9080e9ee360d433693a3a1763bb3397e |
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| Source note | uspto-grants-2012_09 |
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