HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (R)-3'-(Thiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Bromothiophene | HCID 13851 | — |
| Reactant | AR-R-17779 | HCID 5310971 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | (R)-3'-(Thiophen-2-yl)spiro[1-azabicyclo[2.2.2]octan-3,5'-oxazolidin]-2'-one | HCID 9921468 | 47.6% |
Reaction Steps
(S)-Spiro[1-azabicyclo[2.2.2]octan-3,5′-oxazolidin]-2′-one (505 mg, 3.58 mmol), 5-bromothiophene (1.75 g, 10.74 mmol), copper (I) iodide (69 mg, 0.36 mmol) and potassium carbonate (495 mg, 3.58 mmol) were stirred at 120° C. overnight. After cooling to room temperature, the mixture was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the title compound as a yellow solid (450 mg), m/zz 265 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07514567B2 |
| Source dataset | uspto-grants-2009_04 |
| ORD ID | ord-b5f6e47d584b469d8e8a8a9ce697ddd2 |
| Source note | uspto-grants-2009_04 |