Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 9-Borabicyclo(3.3.1)nonane | HCID 78966 | — |
| Reactant | 5-Bromo-2,2-difluoro-1,3-benzodioxole | HCID 2736271 | — |
| Reactant | tert-Butyl 3-methylidenepyrrolidine-1-carboxylate | HCID 15297967 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | N,N-Dimethylformamide--water (1/1) | HCID 21962138 | — |
| Product | HCID 66974052 | HCID 66974052 | 96.7% |
Reaction Steps
A stream of N2 was bubbled through neat 3-methylene pyrrolidine-1-carboxylic acid tert-butyl ester (792 mg, 4.33 mmol) for 15 min before charging the flask with 9-BBN (0.5 M in THF, 8.8 mL). The reaction mixture was heated at reflux for 2.5 h; then cooled to rt. The resultant mixture was then added, via cannula, to a preformed solution consisting of 5-bromo-2,2-difluoro-1,3-benzodioxole (1.01 g, 4.24 mmol), Pd(dppf)Cl2.CH2Cl2 (92 mg), and potassium carbonate (760 mg, 5.50 mmol) in DMF/H2O (10 mL/1 mL). The reaction mixture was heated at 60° C. for 18 h, cooled to rt and poured into water. The pH of the mixture was adjusted to 11 with NaOH (1 N), and extracted with EtOAc (3×). The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound (1.4 g, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08901111B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-6f228b1399c448298ce39470bea8270b |
|---|
| Source note | uspto-grants-2014_12 |
|---|
