CS214286B1 - Process for preparing pyrrolidine derivatives - Google Patents

Process for preparing pyrrolidine derivatives Download PDF

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Publication number
CS214286B1
CS214286B1 CS689380A CS689380A CS214286B1 CS 214286 B1 CS214286 B1 CS 214286B1 CS 689380 A CS689380 A CS 689380A CS 689380 A CS689380 A CS 689380A CS 214286 B1 CS214286 B1 CS 214286B1
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CS
Czechoslovakia
Prior art keywords
trans
pyrrolidine derivatives
preparing pyrrolidine
yields
preparation
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CS689380A
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Czech (cs)
Slovak (sk)
Inventor
Bohuslav Baranek
Bernhard Poitz
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Bohuslav Baranek
Bernhard Poitz
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Application filed by Bohuslav Baranek, Bernhard Poitz filed Critical Bohuslav Baranek
Priority to CS689380A priority Critical patent/CS214286B1/en
Publication of CS214286B1 publication Critical patent/CS214286B1/en

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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Sposob přípravy derivátov pyrrolidínu ako medziproduktu pre přípravu lokál- nych anestetik, dSležitých farmaceutických látok. Vynález rieál přípravu cyklo- hexyl-oyklopentyl-pyrrolidínov z cyklo- hexanolu pomocou kys. brommej a katalytického množstva kyseliny sírovej a vý- tažkami cca 78 %·A process for preparing pyrrolidine derivatives as an intermediate for the preparation of local anesthetics, important pharmaceutical agents. The invention has been directed to the preparation of cyclohexyl-o-cyclopentyl-pyrrolidines from cyclohexanol by means of acid. bromine and catalytic amounts of sulfuric acid and yields of about 78% ·

Description

214 286 1

Vynález sa týká epoeobu derlvátov pyr rodil inu obecného vzorce R-OH-pyrrolldín,kde R je cyklohexyl alebo cyklopentyl.

Eri výrobě lokálnych anestetik typu heptakeinu (Beneše, Borovaneký: δβ. f armáda20. 10, 197j 21. 150, 1952) sa používá ako základná surovina cyklohexanol, ktorá eezoyklohexén, chlórcyklohexanol a epoxid poskytuje Cyldohexylpyrrolidín, medziproduktna výrobu uvedeného lokálneho anestetika.

(I) (II) (III)

Nevýhodou postupu Je, že je velni pracný, vyžaduje dlhá reakdná doby (chlórcyklo-hexanol 36 h., epoxid 7,5 h., piperidinocyklohexanol 11 h. - spolu 54,5 h) a dává nízkovýtažky asi 28 %. Nízké výtažky možno pripísat skutodnoeti, že při reakeii eyklehexénu a kyselinouohlórnou vzniká cis- a trans-izomér chlórcyklohexanol^ pridom sa v reakeii využívá lentrans-izomér. Pokusy s izomerizáciou cis-izoméru boli neúspěšné.

Uvedené nevýhody odstraňuje postup podía nášho vynálezu. Zletilí sne, že při pří-pravě podobných látok je výhodnéjžie použit na přípravu potřebného epoxidu kyselinubrómnu, pretože přitom nevzniká eis- a trans-izomér, ale len trans-izomér bróncyklo-hexanolu a reakcla sa prevádza v jednom reakdnom stupni bez izoláole medsiproduktov IIa III. Reakdná doba sa ekrátl na 16 - 18 hodin, teda na jednu třetinu a výtažky sazvýSla na 78 %. Spotřeba surovin a pracnost je oveía menšia.

Kyselina brómna vzniká z N-brómsukcinimidu podía nasledovnej schénjy (Pieser,Pieser Experimente in Organlc Chemistry str. 91, Goeud. naudno-techn.izd.ehim.lit,Moskva 1960): CHO-C0\ | * - N-— Br + H20 ch2-CO^ CH,-- C0x > | á NH + HOBr

ch2-C0X

N-brómsukcinimid sa po skondení reakcie prevedenia ne pdvodné činidlo.

214 286 1

The present invention relates to the epoeobu of the pyrrolyl derivatives of the formula R-OH-pyrrolidine, wherein R is cyclohexyl or cyclopentyl.

Eri production of local heptakein-type anesthetics (Benes, Borovany: δβ. F army20. 10, 197j 21. 150, 1952) is used as the basic raw material of cyclohexanol, which is cyclohexanol, chlorocyclohexanol and epoxide provides Cyldohexylpyrrolidine, an intermediate for the production of said local anesthetic.

(I) (II) (III)

The disadvantage of the process is that it is laborious, requires a long reaction time (chlorocyclohexanol 36h, epoxide 7.5h, piperidinocyclohexanol 11h - total 54.5h) and yields low yields of about 28%. The low yields can be attributed to the fact that the cis- and trans-isomers of chlorocyclohexanol are added to the cyclo-hexene and acidic acid lentrans-isomer. Isomerization of the cis-isomer was unsuccessful.

These disadvantages are eliminated by the process of the present invention. The adult dreams that when preparing similar substances, it is preferable to use acid to prepare the necessary epoxide because the eis- and trans-isomer is not produced, but only the trans-isomer of bromocyclohexanol and the reaction is carried out in one reaction step without isolation of intermediates IIa III . The reaction time was reduced to 16-18 hours, ie to one third and the yields of carbonate to 78%. Consumption of raw materials and labor is much less.

The bromine acid is formed from N-bromosuccinimide according to the following scheme (Pieser, Pieser Experiment in Organ Chemistry p. 91, Goeud. Naudno-techn.izd.ehim.lit, Moscow 1960): CHO-C0 \ t * - N - Br + H 2 O ch 2 -CO 2 CH 2, -CO x - NH + HOBr

ch2-C0X

The N-bromosuccinimide is not an original reagent upon dissolution of the reaction.

Claims (1)

PREDMET VYNÁLEZUOBJECT OF THE INVENTION Spoaob přípravy derivátov pyrrolidínu obecného Vzarea R-OH-pyrrolidín, kde R je eyklohexyl alebo cyklopentyl, z transbrómcyklohexanolu alebo transbrómcyklopentanolu pósobením 50 %-ného hydroxidu sodného a pyrrolidínu vyznačený tým, že sa transbromcyklohexanol alebo transbrómcyklopentanol připraví posobením kyseliny brómnej v přítomnosti katalytického množstva kyseliny sírovej na cyklohexén alebo cyklopentén.R-OH-pyrrolidine, wherein R is cyclohexyl or cyclopentyl, from trans-bromocyclohexanol or trans-bromocyclopentanol by treatment with 50% sodium hydroxide and pyrrolidine, characterized in that the trans-bromocyclohexanol or trans-bromocyclopentanol is prepared by the amount of trans-bromocyclohexanol or trans-bromocyclopentanol to cyclohexene or cyclopentene.
CS689380A 1980-10-11 1980-10-11 Process for preparing pyrrolidine derivatives CS214286B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CS689380A CS214286B1 (en) 1980-10-11 1980-10-11 Process for preparing pyrrolidine derivatives

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CS689380A CS214286B1 (en) 1980-10-11 1980-10-11 Process for preparing pyrrolidine derivatives

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CS214286B1 true CS214286B1 (en) 1982-04-09

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