Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | 1-Benzyl-2,5-dihydropyrrole | HCID 561506 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 9855817 | HCID 9855817 | 76% |
Reaction Steps
To a solution of 15.9 g (0.1 mol) of 1-benzyl-3-pyrroline, 12.0 g (0.12 mol) of 98% sulfuric acid, and 60.0 g of acetone in a quartz round flask reactor, 45.6 g (0.20 mol) of (NH4)2S2O8 (ammonium peroxydisulfate produced by Mitsubishi Gas Chemical Industry Co., Ltd.) was added with stirring and allowed to react for 5 days at room temperature with irradiation by 500 W Xe lamps (UXL-500D xenon lamp produced by Ushio). 57.9 g (0.3 mol) of 28wt % NaOMe in methanol solution (produced by Katayama Chemical Industry Co., Ltd.) was continuously added to the reaction mixture and stirred for 5 hours under reflux. After completion, acetone and methanol were evaporated under reduced pressure, and extracted with toluene and water. After the solvent was evaporated under reduced pressure, 15.8 g of 1-benzyl-4-methoxy-3-pyrrolidinol (yield 76.0%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06130338 |
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| Source dataset | uspto-grants-2000_10 |
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| ORD ID | ord-e6abefaa060b4914b5d2181ae4c080bb |
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| Source note | uspto-grants-2000_10 |
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