HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-formylthiophene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate | HCID 86648490 | — |
| Reactant | Methyl 5-bromo-3-formylthiophene-2-carboxylate | HCID 86648830 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | Methyl cis(+/-)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-formylthiophene-2-carboxylate | HCID 86648831 | 20.9% |
Reaction Steps
The same operation as in Example (244b) was performed using methyl 5-bromo-3-formylthiophene-2-carboxylate obtained in Example (246b) (974 mg, 3.91 mmol), benzyl cis(±)-(3-methoxypiperidin-4-yl)-carbamate obtained in Example (40b) (1.10 g, 4.16 mmol), palladium acetate (176 mg, 0.78 mmol), BINAP (0.49 g, 0.78 mmol) and cesium carbonate (1.78 g, 5.47 mmol), to obtain 354 mg of the title compound as a yellow oily substance (21%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08536197B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-e7105cf23d7d46ceb8474ab4940ef051 |
| Source note | uspto-grants-2013_09 |