HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chloroacetophenone → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chloroacetophenone | HCID 10757 | — |
| Reactant | (R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate | HCID 86688927 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chloride | HCID 86688928 | 67.9% |
Reaction Steps
2-Chloro-1-phenylethanone (62.1 mg, 0.40 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate (120 mg, 0.36 mmol) in EtOAc (2.4 ml) and acetonitrile (1.2 ml). The pale yellow solution was stirred at room temperature for three days. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=9/1) to collect the title compound (118 mg, 66.9% yield) as an off-white spongy solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748613B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-6a8866aedb5848b7be26458da4bbc8f4 |
| Source note | uspto-grants-2014_06 |