化工社化工社 化学情報印刷レポート · 研究参考用
Tert-Butylamine → oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1(2H)-naphthalenone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Tert-Butylamine | HCID 6385 | — |
| 反応物 | Levobunolol | HCID 39468 | — |
| 反応物 | 5-Hydroxy-1-tetralone | HCID 119921 | — |
| 反応物 | (-)-Epichlorohydrin | HCID 2734062 | — |
| 反応物 | Bunolol, (R)- | HCID 5460339 | — |
| 生成物 | oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1(2H)-naphthalenone | HCID 86748747 | — |
反応手順
The invention relates to a new, industrially advantageous, process for the preparation of the known beta-adrenergic blocking agent, levobunolol, not requiring resolution of racemic bunolol, based on the enantioselective synthesis of an oxiranic intermediate which is then reacted with tert-butylamine. It consists of reacting 5-hydroxy-3,4-dihydro-1(2H)-naphthalenone with (R)-(-)epichlorhydrine in an aprotic solvent, in the presence of a strong base at a temperature of over 90° C., thus obtaining the intermediate chiral oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1-(2H)-naphthalenone with more than 95% optical purity, and then, the intermediate chiral oxirane is reacted with tert-butylamine.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05426227 |
| 出典データセット | uspto-grants-1995_06 |
| ORD ID | ord-b1ed1b450ffe4160b30986771988e595 |
| 出典メモ | uspto-grants-1995_06 |