Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyl acrylate | HCID 15458 | — |
| Reactant | Proline benzyl ester hydrochloride | HCID 2733413 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 86687109 | HCID 86687109 | 79% |
Reaction Steps
Tert-butyl acrylate (5.00 mL) was added to a solution of L-proline benzyl ester hydrochloride salt (1.10 g, 4.54 mmol) and Et3N (632 μL, 4.54 mmol) in tert-butanol (5.00 mL). The reaction was heated to 80° C. for 3 h then and evaporated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (1.20 g, 79%). 1H NMR (300 MHz, CDCl3): 1.43 (9H, s), 1.72-2.00 (3H, m), 2.08 (1H, m), 2.39-2.48 (3H, m), 2.72 (1H, ddd, J 12.2, 8.4, 6.7), 3.00 (1H, dt, J 12.3, 7.8), 3.13 (1H, m), 3.28 (1H, dd, J 8.6, 5.4), 5.13 (1H, d, J 12.3), 5.18 (1H, d, J 12.3), 7.29-7.39 (5H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09139584B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-d7cca862cd464c429201b2aa6d41962f |
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| Source note | uspto-grants-2015_09 |
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