化工社化工社 化学情報印刷レポート · 研究参考用
4-Bromobenzaldehyde → 1,1-Dimethylethyl (2R,6S)-4-[(4-bromophenyl)methyl]-2,6-dimethyl-1-piperazinecarboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-Bromobenzaldehyde | HCID 70741 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | Sodium triacetoxyborohydride | HCID 5049666 | — |
| 反応物 | tert-Butyl (2R,6S)-2,6-dimethylpiperazine-1-carboxylate | HCID 21021901 | — |
| 溶媒 | 1,2-Dichloroethane | HCID 11 | — |
| 生成物 | 1,1-Dimethylethyl (2R,6S)-4-[(4-bromophenyl)methyl]-2,6-dimethyl-1-piperazinecarboxylate | HCID 25224097 | 91.8% |
反応手順
A mixture of 4-bromobenzaldehyde (1.85 g, 10 mmol), 1,1-dimethylethyl (2R,6S)-2,6-dimethyl-1-piperazinecarboxylate (2.15 g, 10 mmol) and sodium triacetoxyborohydride (3.18 g) in 1,2-DCE (35 ml) was stirred at room temperature for 3 days. Saturated aq. NaHCO3 solution was added and the mixture stirred for 30 mins. The product was extracted into EtOAc and the extracts dried (Na2SO4) and concentrated. The residue was dissolved in DCM and treated with PS-hydrazine resin with stirring for 2 h. The resin was removed by filtration and the solvent removed in vacuo. Chromatography (0-40% EtOAc/hexane) gave the title compound (3.52 g). MS (ES): MH+ 383/385.
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-758b8aff5c324789a35f03191e911f1b |
| 出典メモ | uspto-grants-2013_09 |