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Synthesis of (S)- and (R)‑N‑Boc-3-(Trifluoromethyl)piperazines

有机合成与工艺文献分享 2025-07-07 06:36
文章摘要
本文报道了(S)-和(R)-N-Boc-3-(三氟甲基)哌嗪的合成研究。背景方面，已有三种外消旋2-(三氟甲基)哌嗪的合成方法被专利公开。研究目的是开发一种直接利用手性N-Boc保护的3,3,3-三氟丙烷-1,2-二胺(2)和2-氯乙酰氯衍生的酮哌嗪中间体还原的合成路线。研究过程中评估了三种合成路线：路线A因分离过程困难且产率低被放弃；路线B由于亲核三氟甲基化的放大问题被淘汰；最终通过路线C成功建立了3,3,3-三氟-1-硝基丙烯(11)的大规模生产工艺。结论表明，该工艺成功实现了无需色谱纯化的(S)-1和(R)-1对映异构体的多克级合成，具有高度的非对映选择性。
Synthesis of (S)- and (R)‑N‑Boc-3-(Trifluoromethyl)piperazines
查看文献： Development of a Safe and Practical Synthesis of Enantiomerically Pure (S)- and (R)-N-Boc-3-(Trifluoromethyl)piperazines Enabled by Aza-Michael Addition of Optically Pure 4-Phenyl-2-Oxazolidinone to 3,3,3-Trifluoro-1-Nitropropene
查看期刊： Organic Process Research & Development
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Synthesis of (S)- and (R)‑N‑Boc-3-(Trifluoromethyl)piperazines
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