Convenient and Inexpensive Synthesis of (1R,2R)‐ trans‐1‐Amino‐6‐nitroindan‐2‐ol
作者： Sergei?I. Kozhushkov , Dmitrii?S. Yufit , Armin de?Meijere
关键词:
摘要: Racemic trans-1-amino-6-nitroindan-2-ol (rac-1) has been prepared in five steps from inexpensive indene (7) 96% overall yield. The key step was a direct nitration of the known trans-1-aminoindan-2-ol (rac-9) which gave sulfuric acid mono-(rac-trans-1-amino-6-nitroindan-2-yl) ester (rac-10) quantitative latter quantitatively converted into rac-1 by treatment with aqueous 6 N HCl and then ammonia solutions. same transformations (1R,2R)-9 [prepared deracemization rac-9 (−)-dibenzoyl-L-tartaric (DBT)] proceeded without loss optical activity. Deracemization applying (+)-(S)-L-mandelic (MA) furnished (1R,2R)-1 (1S,2S)-1 34 17% yield, respectively, e.e. ≥ 98 97.6%, respectively. Procedures for recycling chiral auxiliaries DBT MA are also described. structures intermediates were confirmed X-ray crystal structure analysis.
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