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Diethyl Oxalate → 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diethyl Oxalate | HCID 7268 | — |
| 反応物 | Lithium diisopropylamide | HCID 2724682 | — |
| 反応物 | (4-(4-Methylpiperidin-1-yl)-3-nitrophenyl)methanol | HCID 28963353 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 3-(2-Nitro-3-piperidin-1-yl-phenyl)-2-oxo-propionic acid ethyl ester | HCID 59796771 | — |
反応手順
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).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07790724B2 |
| 出典データセット | uspto-grants-2010_09 |
| ORD ID | ord-5b64d57edf6740d3b81f185e2a7dd28d |
| 出典メモ | uspto-grants-2010_09 |