当前位置:
X-MOL 学术
›
J. Heterocycl. Chem.
›
论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Efficient preparation of (S)-2-(3,5-dimethylphenyl)pyrrolidine via a recycle process of resolution
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2022-10-04 , DOI: 10.1002/jhet.4580 Chuanqi Duan 1 , Siju Bi 1 , Ting Tian 1 , Ting Zhou 1 , Kuaile Lin 1 , Weicheng Zhou 1
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2022-10-04 , DOI: 10.1002/jhet.4580 Chuanqi Duan 1 , Siju Bi 1 , Ting Tian 1 , Ting Zhou 1 , Kuaile Lin 1 , Weicheng Zhou 1
Affiliation
![]() |
(S)-2-(3,5-dimethylphenyl)pyrrolidine((S)-1), a key intermediate in the synthesis of aticaprant, was effectively prepared via a recycle process of resolution/racemization. The desired (S)-1 was obtained by resolution of its racemate with D-tartaric acid and some alkaline conditions were screened to racemize the undesired (R)-1 in the resolution mother liquor, and the best (in DMSO with KOH) was identified. Finally, the desired freebase (S)-1 was obtained in a yield of 63.6% with excellent enantioselectivity (98.7% ee) after three times of recycle process.
中文翻译:
通过拆分循环过程高效制备 (S)-2-(3,5-二甲基苯基) 吡咯烷
( S )-2-(3,5-二甲基苯基)吡咯烷(( S )- 1 )是合成阿替卡普兰的关键中间体,通过拆分/外消旋的循环过程有效制备。用D-酒石酸拆分其外消旋体得到所需的( S )- 1 ,筛选碱性条件使拆分母液中不需要的( R )- 1外消旋,最好的(在DMSO和KOH中)确定。最终,经过3次循环过程,以63.6%的收率和优异的对映选择性(98.7% ee)获得了所需的游离碱(S)- 1 。
更新日期:2022-10-04
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
通过拆分循环过程高效制备 (S)-2-(3,5-二甲基苯基) 吡咯烷
( S )-2-(3,5-二甲基苯基)吡咯烷(( S )- 1 )是合成阿替卡普兰的关键中间体,通过拆分/外消旋的循环过程有效制备。用D-酒石酸拆分其外消旋体得到所需的( S )- 1 ,筛选碱性条件使拆分母液中不需要的( R )- 1外消旋,最好的(在DMSO和KOH中)确定。最终,经过3次循环过程,以63.6%的收率和优异的对映选择性(98.7% ee)获得了所需的游离碱(S)- 1 。