HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → 3-(((4-Methoxyphenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | 2-(Chloroacetyl)thiophene | HCID 2757925 | — |
| Reactant | (4-Methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate | HCID 70925768 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(((4-Methoxyphenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride | HCID 70673758 | 31.2% |
Reaction Steps
To a solution of (4-methoxyphenyl)(phenyl)methyl quinuclidine-3-carboxylate (37 mg, 0.10 mmol) in EtOAc (1.5 ml), 2-chloro-1-(thiophen-2-yl)ethanone (19 mg, 0.12 mmol) was added. Acetonitrile was added until complete dissolution, and the reaction was stirred at room temperature overnight. The organic solvents were removed under vacuum, and the residue was purified by flash chromatography (DCM/MeOH=9/1) to obtain 3-(((4-methoxyphenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (16 mg, mixture of diastereoisomers).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08604015B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-ec50e39e0d854d449ab0d0f9d774be58 |
| Source note | uspto-grants-2013_12 |