Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(Cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 15486611 | — |
| Reactant | HCID 18331463 | HCID 18331463 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 117778323 | HCID 117778323 | 94.2% |
Reaction Steps
Tert-butyl N-[(3-bromophenyl)methyl]-N-tert-butoxycarbonylcarbamate (5.40 g) was dissolved in a mixed solvent of toluene (150 mL), ethanol (100 mL), and water (100 mL). To the solution, 2-(cyclopenten-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.26 g), tetrakis(triphenylphosphine) palladium complex (1.62 g), and sodium carbonate (4.45 g) were added at room temperature, and the mixture was then heated to reflux for 19 hours. The reaction solution was cooled to room temperature, and ethyl acetate was then added thereto for separation into organic and aqueous layers. The organic layer was washed with water and concentrated under reduced pressure, and the obtained residue was then purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate) to obtain the title compound (4.92 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206168B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-29612bae8bcc4f438608f252efe44c9a |
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| Source note | uspto-grants-2015_12 |
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