Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Oxazole | HCID 9255 | — |
| Reactant | Magnesium Bromide | HCID 82241 | — |
| Reactant | HCID 24960700 | HCID 24960700 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59178877 | HCID 59178877 | — |
Reaction Steps
A −10° C. solution of MgBr2 (37 mg; 0.202 mmol) in THF (1 mL) was treated with nBuLi (0.333 mL; 1.82M; 0.606 mmol) The solution was stirred at −10° C. for 1 hr. A solution of oxazole (42 mg; 0.606 mmol) in THF (0.5 mL) was added and the solution was stirred at 25° C. for 2 hr. This solution was added to a refluxing solution of tert-butyl 1′-(4-iodophenyl)-4,4′-bipiperidine-1-carboxylate (285 mg; 0.606 mmol) and PdCl2(dppf) (495 mg; 0.606 mmol) in THF (4 mL). The mixture was refluxed 1 hr. The reaction was partitioned between CH2Cl2 and water. The organic was dried over magnesium sulfate, filtered and evaporated to a solid. The solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH) to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08445499B2 |
|---|
| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-7169cbd60e4343988a1459e3da388448 |
|---|
| Source note | uspto-grants-2013_05 |
|---|
