Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 1,1-Dimethylethyl 2-cyanobutanoate | HCID 53356472 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58820945 | HCID 58820945 | — |
Reaction Steps
To a solution of 2-cyano-butyric acid tert-butyl ester (810 mg, 4.79 mmoL) and DBU (1.4 mL, 9.58 mmol) in DMF (5 mL) was added iodomethane (1.2 mL, 19.20 mmol) dropwise at 0° C. The resulting mixture was heated to 40° C. for 24 hours. After cooling to room temperature, H2O (50 mL) and EtOAc (50 mL) were added. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% EtOAc/hexanes) to give the title compound in 650 mg. 1H NMR (CDCl3, 200 MHz): δ=2.05-1.6 (m, 2H), 1.53 (s, 3H), 1.50 (s, 9H), 1.07 (t, 3H, J=7.3 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409892B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-edae5a64dc1849c4adb485ad90103a16 |
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| Source note | uspto-grants-2016_08 |
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