Authors Ma, QN; Yang, XD; Lei, XS; Lin, GQ in ROYAL SOC CHEMISTRY published article about ASYMMETRIC-SYNTHESIS; QUATERNARY CARBON; ALPHA(2C)-ADRENOCEPTOR ANTAGONIST; STEREOSELECTIVE CONSTRUCTION; REDUCTION; DELTA(3)-2-HYDROXYBAKUCHIOL; ACIDS in [Ma, Qiaoning; Lei, Xinsheng; Lin, Guo-Qiang] Fudan Univ, Inst Biomed Sci, 826 Zhangheng Rd, Shanghai 201203, Peoples R China; [Ma, Qiaoning; Lei, Xinsheng; Lin, Guo-Qiang] Fudan Univ, Sch Pharm, 826 Zhangheng Rd, Shanghai 201203, Peoples R China; [Yang, Xiaodi; Lin, Guo-Qiang] Shanghai Univ Tradit Chinese Med, Expt Ctr Sci & Technol, Shanghai 201203, Peoples R China; [Lin, Guo-Qiang] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China in 2019.0, Cited 32.0. COA of Formula: C7H5NO4. The Name is 4-Nitrobenzoic acid. Through research, I have a further understanding and discovery of 62-23-7
The preparation of ORM-10921, a selective (2C)-adrenoceptor antagonist with promising anti-psychotic properties, was successfully achieved using asymmetric -alkylation of ,-unsaturated imide and Bischler-Napieralski cyclization/asymmetric reduction as the key steps. When the tetracyclic iminium 11S was used in the reduction, the diastereo-selectivity was poor, from which four stereoisomers of ORM-10921 were obtained, respectively. However, the diastereoselectivity could be significantly improved (with dr up to >97:3) when the tricyclic imine substrate 19S was applied in this reduction, suggesting an additional chelation from the side-chain methoxy group in the transition state. According to this protocol, ORM-10921 was accomplished in a highly enantioselective manner. In addition, two analogs 26Aa and 26Ba were prepared using this novel method, and the absolute configurations were unambiguously assigned by single crystal X-ray crystallography.
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Reference:
Phthalazine – Wikipedia,
,Phthalazine | C8H6N2 – PubChem