Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-04-05
1999-12-21
McKane, Joseph K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548566, C07D20712
Patent
active
060051191
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing a pyrrolidine derivative of the general formula (2): ##STR2## (wherein R represents a 1-cyano-1,1-diphenylmethyl, 1-carbamoyl-1,1-diphenylmethyl, n-butyryloxy, methanesulfonyloxy or p-toluenesulfonyloxy group) or a salt thereof, which is useful as an intermediate for the synthesis of medicinals, agrochemicals and other chemicals.
BACKGROUND ART
As a process for producing the above-mentioned pyrrolidine derivative of general formula (2) or a salt thereof using compounds of the general formula (1): ##STR3## (wherein R is as defined above) as a starting material, a process is known (Japanese Kokai Publication Sho-61-100563) which comprises once synthesizing methyl 3-(1-cyano-1,1-diphenylmethyl)-1-pyrrolidinecarboxylate starting with 1-benzyl-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine and then converting the former to 3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine. However, this process involves long steps and complicated operation and gives low yields, hence can hardly be said to be an industrial production process.
Another process is also known (Japanese Kokoku Publication Hei-07-72171) for producing 3-(1-carbamoyl-1,1-diphenylmethyl)-pyrrolidine by subjecting 1-benzyl-3-(1-carbamoyl-1,1-diphenylmethyl)-pyrrolidine to hydrogenolysis using palladium-carbon. However, it uses a large amount of palladium, which is expensive, and requires a long reaction time. Thus, it has problems as an industrial production process from the viewpoints of economy and productivity.
Furthermore, no process is known for producing 3-methanesulfonyloxypyrrolidine or a salt thereof by debenzylating 1-benzyl-3-methanesulfonyloxypyrrolidine, for producing 3-p-toluenesulfonyloxypyrrolidine or a salt thereof by debenzylating 1-benzyl-3-p-toluenesulfonyloxypyrrolidine, or for producing 3-n-butyryloxypyrrolidine or a salt thereof by debenzylating 1-benzyl-3-n-butyryloxypyrrolidine.
Accordingly, the development of a process for producing the above-mentioned pyrrolidine derivative of general formula (2) or a salt thereof in a simple and economical manner and with good productivity and high yields by debenzylating the above-mentioned compound of general formula (1) has been desired.
SUMMARY OF INVENTION
In view of the foregoing, it is an object of the present invention to provide a process for producing the above-mentioned pyrrolidine derivative of general formula (2) or a salt thereof in a simple and economical manner and with good productivity and high yields.
The present invention consists in a process for producing a pyrrolidine derivative of the general formula (2): ##STR4## (wherein R is as defined above) or a salt thereof which comprises subjecting a compound of the general formula (1): ##STR5## (wherein R is as defined above) to hydrogenolysis using a metal catalyst in the presence of at least one protic acid selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid, p-toluenesulfonic acid, methanesulfonic acid, acetic acid, n-butyric acid, trifluoroacetic acid and oxalic acid.
DETAILED DISCRIPTION OF THE INVENTION
The present invention is described in detail in the following.
The above-mentioned compound of general formula (1) which is to be used in the process of the present invention can be produced by the processes described, for example, in Japanese Kokai Publications Sho-61-100563, Hei-01-113365, Hei-01-141600 and Hei-01-143852.
The protic acid to be used in accordance with the present invention is at least one species selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid, p-toluenesulfonic acid, methanesulfonic acid, acetic acid, n-butyric acid, trifluoroacetic acid and oxalic acid. Among them, hydrochloric acid, sulfuric acid and oxalic acid are preferred.
It is sufficient that said protic acid be used in an amount of about 1 equivalent relative to the above-mentioned compound of general formula (1), which is the starting material.
In the practice of the present invention, said protic ac
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Naylor et al, "4-[(Alkylamino)methyl]furo[3,2-c]pyridines: A New Series of Selective kReceptor Agonists", Journal of Medicinal Chemistry, vol. 37, No. 14, 1994, pp. 2138-2144.
Furuta Takeshi
Kan Kazunori
Mori Natsuki
Yoshida Noritaka
Kaneka Corporation
McKane Joseph K.
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