HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → (1R)-1'-({1-[4-(Pyrrolidin-1-ylcarbonyl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | (1R)-1'-{[1-(4-bromophenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one | HCID 66661876 | — |
| Catalyst | Molybdenum carbonyl (Mo(CO)6) | HCID 98885 | — |
| Catalyst | trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II) | HCID 11104995 | — |
| Product | (1R)-1'-({1-[4-(Pyrrolidin-1-ylcarbonyl)phenyl]cyclopropyl}carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one | HCID 66662255 | 79% |
Reaction Steps
A mixture of (1R)-1′-{[1-(4-bromophenyl)cyclopropyl]carbonyl}-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (68.0 mg, 0.000165 mol, example 238), pyrrolidine (42 μL, 0.00049 mol), molybdenum hexacarbonyl (44 mg, 0.00016 mol), trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II) (16 mg, 0.000016 mol) and 1,8-diazabicyclo[5.4.0] undec-7-ene (76 μL, 0.00049 mol) (DBU) in anhydrous tetrahydrofuran (2.0 mL, 0.025 mol) in a microwave vial was irradiated with microwaves to 150° C. for 30 minutes. The reaction mixture was filtered. The filtrate was purified by prep-HPLC to afford the product as a solid (55.9 mg, 79% in yield). LC/MS (M+H+)=431.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07776874B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-39c2631f60514bbfbc96d19f8f906d55 |
| Source note | uspto-grants-2010_08 |