HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,2-Dimethoxypropane → 2-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,2-Dimethoxypropane | HCID 6495 | — |
| Reactant | D-Camphorsulfonic Acid | HCID 65617 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine | HCID 69758731 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine | HCID 69759918 | 100% |
Reaction Steps
A mixture of 2.5 g of 2-benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine, 2.3 g of dl-10-camphorsulfonic acid, 20 ml of 2,2-dimethoxypropane and 5.0 ml of N,N-dimethylformamide was stirred at room temperature overnight. Aqueous saturated sodium bicarbonate was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, and the solvent was removed. Then, the residue was subjected to filtration through silica gel and eluted with ethyl acetate, to give 2.87 g of the target compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06599917B1 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-141347c0d4224e4d8930515a0805b62e |
| Source note | uspto-grants-2003_07 |