- Method for preparing (1R, 3S)-3-aminocyclopentanol hydrochloride
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The invention discloses a method for preparing (1R, 3S) 3-aminocyclopentanol hydrochloride, belongs to the field of organic chemical synthesis, and provides a process route to overcome the defects ofhigh price, difficulty in chiral control and the like in the prior art. The process route comprises the following steps: 1) oxidizing tert-butyl carbonate hydroxylamine into tert-butyl carbonate nitrosyl under the catalysis of copper chloride and 2-ethyl-2-oxazoline, then carrying out a hetero Diels-Alder reaction with cyclopentadiene in situ; 2) selectively reducing nitrogen-oxygen bonds in a zinc powder-acetic acid reaction system; 3) under the catalysis of lipase, reacting with vinyl acetate to optically and selectively realize chiral resolution; 4) reducing double bonds through palladium carbon hydrogenation; 5) under the alkaline condition of lithium hydroxide-methanol, performing deacetylation protection; and 6) removing tert-butyl carbonate protection in a hydrogen chloride isopropanol acid solution prepared from acetyl chloride and isopropanol in situ, and forming hydrochloride in situ to obtain a target product. The synthetic method has the beneficial effects that the synthetic method has the characteristics of novel and short route, high optical purity, low cost and the like.
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- Preparation method of (1R,3S)-3-amino cyclopentanol hydrochloride
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The invention provides a preparation method of (1R,3S)-3-amino cyclopentanol hydrochloride. A urea peroxide-trifluoroacetic anhydride system is adopted as an oxidizing agent, and a compound I is subjected to oxidation reaction so as to generate a compound II and a compound II', so that the use of an oxidizing agent with high price and big risk is avoided. Hydrogen chloride obtained through esterification reaction of isopropanol and an acyl chloride compound is subjected to de-protection reaction with a compound III, so that the process stability is good compared with the way of directly feeding hydrogen chloride and carrying out de-protection reaction on the hydrogen chloride and the compound III, the condition that the (1R,3S)-3-amino cyclopentanol hydrochloride can be smoothly separatedout from a reaction solution is ensured, and the method is convenient to operate and friendly to the work environment. In addition, the preparation method provided by the invention is high in productyield and purity, low in production cost, high in safety, simple to operate, and suitable for large-scale production.
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Paragraph 0080; 0081; 0085; 0086; 0089; 0090; 0093; 00094
(2018/12/02)
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- Preparation and evaluation of 1,3-diaminocyclopentane-linked dihydropyrimidinone derivatives as selective α(1a)-receptor
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Several 1,3-diaminocyclopentane linked α(1a)-receptor antagonists were prepared using a divergent chemical strategy that allows for rapid analysis of all stereochemical permutations for their effect on α1-receptor binding. (C) 2000 Published by Elsevier Science Ltd.
- Barrow, James C.,Glass, Kristen L.,Selnick, Harold G.,Freidinger, Roger M.,Chang, Raymond S.L.,O'Malley, Stacey S.,Woyden, Carla
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p. 1917 - 1920
(2007/10/03)
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