Resolution of racemic reticuline and racemization of its enantiomers |
|||||||
| 申请号 | US38418573 | 申请日 | 1973-07-31 | 公开(公告)号 | US3894027A | 公开(公告)日 | 1975-07-08 |
| 申请人 | MERCK & CO INC; | 发明人 | SOHAR PAUL; SCHOENEWALDT ERWIN F; | ||||
| 摘要 | Racemic reticuline is resolved by forming a crystalline diastereomeric acid salt with a mandelic acid enantiomer. The reticuline enantiomers are racemized by treatment with a reduced noble metal or noble metal oxide catalyst. (-)-Reticuline is a valuable intermediate useful in the synthesis of thebaine, and (+)-reticuline is useful as a precursor of pallidine, sinoacutine, coreximine, and the berberine alkaloids. | ||||||
| 权利要求 | 1. THE PROCESS WHICH COMPRISES THE STEPS OF REACTING (+-) -RETICULINE WITH MANDELIC ACID ENANTIOMER IN A SUITABLE SOLVENT MEDIUM, SEEDING THE RESULTING REACTION MIXTURE WITH A CRYSTALLINE DIASTEREOMERIC SALT OF THE ENANTIOMERIC ACID AND A RETICULINE ENANTIOMER, AND SEPARATING AND RECOVERING THE CRYSTALLINE DIASTEREOMERIC SALT OF THE ENANTIOMERIC ACID AND THE RETICULINE ENANTIOMER CORRESPONDING TO SAID SEEDING CRYSTALLINE DIASTEREOMERIC SALT. 2. The process of claim 1 in which the crystalline diastereomer is (-)-reticuline-(-)-mandelate. 3. The process of claim 1 in which the crystalline diastereomer is (-)-reticuline-(+)mandelate. 4. The process of claim 1 in which the crystalline diastereomer is (+)-reticuline-(-)mandelate. 5. The process of claim 1 in which the crystalline diastereomer is (+)-reticuline-(+)-mandelate. 6. A salt of a reticuline enantiomer and a mandelic acid enantiomer. 7. (-)-Reticuline-(-)-mandelate. 8. (-)-Reticuline-(+)-mandelate. 9. (+)-Reticuline-(-)-mandelate. 10. (+)-Reticuline-(+)-mandelate. 11. The process according to claim 1 in which the separated crystalline diastereomer is treated with an alkali base and the reticuline enantiomer is recovered. 12. The process of racemizing a reticuline enantiomer or an acid salt thereof which comprises the step of reacting said enantiomer or a salt thereof with a reduced platinum or platinum oxide catalyst. 13. The process according to claim 12 wherein the reticuline free base is reacted. 14. The process of claim 12 wherein the hydrochloride salt of the reticuline enantiomer is reacted. |
||||||
| 说明书全文 | |||||||
QQ群二维码
意见反馈
意见反馈