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Diethyl Malonate → Diethyl {4-[((3S)-3-methyl-4-{[(phenylmethyl)oxy]carbonyl}-1-piperazinyl)methyl]phenyl}propanedioate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Diethyl Malonate | HCID 7761 | — |
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | 2-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenyl | HCID 2734937 | — |
| 反応物 | Phenylmethyl (2S)-4-[(4-bromophenyl)methyl]-2-methyl-1-piperazine Carboxylate | HCID 25224210 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | Diethyl {4-[((3S)-3-methyl-4-{[(phenylmethyl)oxy]carbonyl}-1-piperazinyl)methyl]phenyl}propanedioate | HCID 25223896 | 60.4% |
反応手順
A mixture of D6 (1.62 g, 4 mmol), diethyl malonate (0.73 ml, 4.8 mmol), palladium (II) acetate (27 mg, 0.12 mmol), potassium phosphate (1.95 g, 2.3 mmol) and bis(1,1-dimethylethyl)(2′-methyl-2-biphenylyl)phosphane (83 mg, 0.264 mmol) in 1,4-dioxane (20 ml) were refluxed together under argon for ˜20 h. The mixture was filtered through Celite® and concentrated. Chromatography (0-40% EtOAc/hexane) gave the title compound as a clear oil (1.165 g). MS (ES): MH+ 483.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08536182B2 |
| 出典データセット | uspto-grants-2013_09 |
| ORD ID | ord-f151d5cad7ab436fa47c85fd91e4ea07 |
| 出典メモ | uspto-grants-2013_09 |