Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Benzimidazole | HCID 5798 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamine | HCID 13822957 | — |
| Reactant | HCID 66661764 | HCID 66661764 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | HCID 66662542 | HCID 66662542 | — |
Reaction Steps
To a solution of 1′-{[1-(4-bromophenyl)cyclobutyl]carbonyl}-3H-spiro[furo[3,4-c]pyridine-1,3′-pyrrolidin]-3-one (30 mg, 0.00007 mol), and 1H-benzimidazole (0.010 g, 0.000087 mol) in toluene (0.5 mL, 0.005 mol) and N,N-dimethylformamide (0.5 mL, 0.006 mol), were added (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (2.1 mg, 0.000014 mol), copper(I) iodide (1 mg, 0.000007 mol), and potassium carbonate (21.1 mg, 0.000152 mol), and the mixture was stirred at 120° C. overnight. The reaction mixture was then filtered and the filtrate was diluted with methanol. The product was purified using prep-HPLC followed by chiral HPLC. LC-MS: 465.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08058288B2 |
|---|
| Source dataset | uspto-grants-2011_11 |
|---|
| ORD ID | ord-3a7f0c5cd8f7459a842584d1f6a08b6f |
|---|
| Source note | uspto-grants-2011_11 |
|---|
