Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| Reactant | tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate | HCID 49783269 | — |
| Reactant | (S)-tert-butyl 2-(4,5-diiodo-1H-imidazol-2-yl)-pyrrolidine-1-carboxylate | HCID 59449990 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178451935 | HCID 178451935 | 99% |
Reaction Steps
A mixture of 5 (630 mg, 1.53 mmol), 6 (520 mg, 1.53 mmol), Pd (PPh3)2Cl2 (56 mg, 0.080 mmol) and CuI (8 mg, 0.04 mmol), P(t-Bu)3 (1.1 mL, 0.31 mmol), piperidine (1.05 mL, 4.60 mmol) in DMF (20 mL) was stirred at 40° C. for 12 h. The reaction mixture was partitioned between H2O and DCM. The organic layer was washed with H2O (4×50 mL) and brine (15 mL), dried over anhydrous Na2SO4, filtered and then concentrated in vacuo. The residue was purified by silica gel chromatography (DCM/MeOH=50/1 (v/v)) to afford 7 (550 mg, 50% yield) as a pale yellow solid. LC-MS (ESI) m/z 623.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08865756B2 |
|---|
| Source dataset | uspto-grants-2014_10 |
|---|
| ORD ID | ord-9daf7b283903470792e61a9c1d5fb06d |
|---|
| Source note | uspto-grants-2014_10 |
|---|
