HuagongsheHuagongshe Chemistry Print Report · For research reference only
Di-tert-butyl dicarbonate → Ethyl 5-[2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-2-thiophenecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | Ethyl 5-(2-cyanophenyl)thiophene-2-carboxylate | HCID 68705066 | — |
| Catalyst | Nickel | HCID 935 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | Ethyl 5-[2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-2-thiophenecarboxylate | HCID 59463267 | 86.1% |
Reaction Steps
To a slurry of ethyl 5-(2-cyanophenyl)thiophene-2-carboxylate (1.09 gm 4.24 mmol) in MeOH (8 mL) was added (BOC)2O (1.11 g, 5.08 mmol) and Raney Nickel (3.6 mL). The reaction mixture was allowed to stir at rt under an atmosphere of hydrogen overnight and then filtered through celite. The filtrate was concentrated and the residue was purified by column chromatography to give ethyl 5-(2-{[(tert-butoxycarbonyl)-amino]methyl}phenyl)thiophene-2-carboxylate (1.32 g, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07795249B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-b4400d6d0b4c41419b9e81927282f9f3 |
| Source note | uspto-grants-2010_09 |