HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl Bromide → tert-butyl 5-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | 1,1-Dimethylethyl octahydro-2H-pyrrolo(3,4-c)pyridine-2-carboxylate | HCID 23282882 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-butyl 5-benzylhexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate | HCID 68725101 | 98.4% |
Reaction Steps
0.777 g of benzylbromide (4.54 mmol) were added dropwise to a mixture of 1.028 g of commercially available tert-butyl hexahydro-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (4.54 mmol), 1.883 g potassium carbonate (13.62 mmol) and a spatula tip of 18-crown-6 in 25 ml of tetrahydrofurane. The reaction mixture was stirred for 16 h at room temperature, filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane, the organic layer was washed with water, dried over magnesium sulfate, filtered and concentrated to yield 1.413 g of product that was used in the subsequent step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08440694B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-f76916d2951a4dfdac6646c7cc459900 |
| Source note | uspto-grants-2013_05 |