HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethyl Oxalate → 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethyl Oxalate | HCID 7268 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | (4-(4-Methylpiperidin-1-yl)-3-nitrophenyl)methanol | HCID 28963353 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester | HCID 59796771 | — |
Reaction Steps
A solution of 1-(3-methyl-2-nitro-phenyl)-piperidine (i) in THF is treated with lithium diisopropylamide (“LDA”) (1 eq), followed by diethyl oxalate (1.05 eq), at 0° C. The reaction is allowed to warm to room temperature over 90 min. The reaction is diluted with water and ether, partitioned, and the aqueous layer is washed with ether. The combined organic layers are dried over MgSO4, filtered and concentrated. Chromatography gives 3-(2-nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester (ii).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07790724B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-5b64d57edf6740d3b81f185e2a7dd28d |
| Source note | uspto-grants-2010_09 |