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Synthetic method of R-structured Rolipram

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve problems such as difficult industrialization, and achieve the effect of simple post-processing, low cost and high yield

Inactive Publication Date: 2010-06-23
JIAXING EPOCHEM PHARMTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0031] In summary, in recent decades, although there have been many reports on the synthesis of R-noprilland, there are unfavorable factors that are difficult to industrialize.

Method used

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Embodiment 1

[0059] Step: in the 100ml there-necked flask, add dichloromethane (60ml), then (E)-2-(cyclopentyloxy)-1-methoxyl group-4-(2-nitrovinyl)benzene ( 10 g, 0.043 mol) and diethyl malonate (8.3 g, 0.052 mol) were added. Under nitrogen atmosphere, add chiral catalyst nickel(II) bromide-bis[(S,S)-N,N'-dibenzylcyclohexyl-1,2-diamine] complex (0.19mg, 0.2mmol) , Reacted for 6 hours at 0 degrees. The solvent was removed under reduced pressure to obtain 14.5 g of white solid (yield: 85.29%). Melting point 94-96 ℃; NMR spectrum (500MHz, CDCl3) δH 6.78 (d, J=8.0, 1H, Ar-H), 6.74-6.70 (m, 2H, Ar-H), 4.87 (dd, J= 13.0, 5.2, 1H, CHAHB-NO2), 4.82 (dd, J=13.0, 9.0, 1H, CHAHB-NO2), 4.73 (app.qd, J=9.3, 3.0, 1H, OCH(CH2)2), 4.15 (app.dt, J=9.0, 5.2, 1H, Ar-*CH), 3.84 (d, J=9.0, 1H, CH-*C), 3.80(s, 3H, OCH3), 3.75(s, 3H, OCH3), 3.57(s, 3H, OCH3), 1.97-1.88(m, 2H, cyclopentyl-H), 1.87-1.76(m, 4H, cyclopentyl-H), 1.65-1.56(m, 2H, cyclopentyl-H ); mass spectrum m / z (CI+) 413 (100%, MNH4+). Optic...

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Abstract

The invention relates to a synthetic method of R-structured Rolipram which is synthesized by using isovanillin as starting raw materials and through six steps of reactions of cyclopentylation, addition reaction, asymmetric Michael addition reaction, reduction ring closing reaction, decarboxylation and cyclization reaction in a stereoselectivity way. The asymmetric synthetic method of the R-structured Rolipram has the advantages of high yield, high enantiomer excess, mild reaction condition, simple and convenient posttreatment, low cost and the like, thereby being a synthetic route with industrialized prospect.

Description

technical field [0001] The present invention relates to a synthesis method of noprillan, in particular to a stereoselective synthesis method of R configuration noprillan. Background technique [0002] Nopriram, (Rolipram, formerly known as ME-3167, ZK-62711, Adeo, etc.), chemical name: 4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone, CAS: 61413-54- 5. Developed by Schering AG, it is a phosphodiesterase IV (PDE4) inhibitor and an anti-inflammatory drug that can be used to treat a variety of nervous system and respiratory diseases, such as: depression, mental disorders, autoimmune diseases , multiple sclerosis, and chronic obstructive pulmonary disease (COPD). [0003] [0004] There is a chiral center in the structure of Noprillan, and there is a pair of enantiomers. The current clinical use is still a racemate. According to literature reports, the physiological activity of the R-isomer is that of the S-isomer. 20 times. In recent years, with the research and pro...

Claims

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Application Information

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IPC IPC(8): C07D207/26
Inventor 葛承胜韩志唐飞宇王小东
Owner JIAXING EPOCHEM PHARMTECH
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