Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 21350223 | HCID 21350223 | — |
| Reactant | HCID 21942282 | HCID 21942282 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 21350205 | HCID 21350205 | 54.5% |
Reaction Steps
3.6 g of 2-benzyl-3-methoxymethyloxy-6-iodopyridine (Production Example 12), 1.5 g of (3R,4R)-3,4-dimethylmethylenedioxy-2-pyrrolidinone synthesized by a method known in literature (J. Org. Chem., 1969, 34, 675), 1.1 g of cuprous iodide and 3.3 g of potassium carbonate were suspended in 20 ml of 1-methyl-2-pyrrolidinone, followed by heating stirring at 140° C. for 20 minutes in an oil bath in a nitrogen atmosphere. After cooling as it was, ethyl acetate and aqueous ammonia were added thereto, and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate anhydride and the solvent was removed. The residue was subjected to silica gel column chromatography using 20-50% ethyl acetate/hexane as an eluent for separation and purification, to give 2 g of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06599917B1 |
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| Source dataset | uspto-grants-2003_07 |
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| ORD ID | ord-57b576ced1024ed5bcef832d8baf1dec |
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| Source note | uspto-grants-2003_07 |
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