Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-04-05
2002-12-24
Owens, Amelia (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06498258
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative and a production process therefor, as well as to production processes for a N-substituted-3-aminomethyltetrahydrofuran-2-one derivative, for an 3-acetyl-3-aminomethyltetrahydrofuran-2-one derivative and for an 3-aminomethyltetrahydrofuran-2-one derivative using the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative as a starting material.
2. Description of the Related Art
To produce an analogous compound to 3-aminomethyltetrahydrofuran-2-one, Japanese Unexamined Patent Application Publication No. 7-60131 discloses a process in which 3-methylenetetrahydro-2-(3H)-furanone is allowed to react with diethylamine in the presence of an inorganic compound and thereby yields a N,N-diethyl-aminomethyltetrahydrofuran-2-one. However, the prepared N,N-diethyl-aminomethyltetrahydrofuran-2-one cannot yield 3-aminomethyltetrahydrofuran-2-one by a simple reaction, which 3-aminomethyltetrahydrofuran-2-one is practically used as a pharmaceutical intermediate.
SUMMARY OF THE INVENTION
Accordingly, an object of the present invention is to provide a novel 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative that is useful for the preparation of an 3-aminomethyltetrahydrofuran-2-one derivative, as well as to provide a production process for the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative.
Another object of the present invention is to provide production processes for a N-substituted-3-aminomethyltetrahydrofuran-2-one derivative and for an 3-acetyl-3-aminomethyltetrahydrofuran-2-one derivative, which are useful for the preparation of such an 3-aminomethyltetrahydrofuran-2-one derivative.
A further object of the present invention is to provide a process for efficiently producing an 3-aminomethyltetrahydrofuran-2-one derivative by a simple reaction.
After intensive investigations to achieve the above objects, the present inventors have found that such an 3-aminomethyltetrahydrofuran-2-one derivative can easily be obtained from a novel 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative. The present invention has been accomplished based on these findings.
Specifically, the present invention provides, in an aspect, an 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by following Formula (1):
wherein R
1
, R
2
and R
3
are the same or different and are each a hydrogen atom or an aliphatic hydrocarbon group; and R
4
and R
5
are the same or different and are each a hydrogen atom or an arylmethyl group which may have a substituent, where at least one of R
4
and R
5
is an arylmethyl group which may have a substituent.
In another aspect, the present invention provides a process for producing the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (1). The process includes the step of subjecting an 3-acetyltetrahydrofuran-2-one derivative represented by following Formula (2):
wherein R
1
, R
2
and R
3
are the same or different and are each a hydrogen atom or an aliphatic hydrocarbon group, to aminomethylation by a reaction with formaldehyde or a polymer thereof and a primary or secondary amine represented by following Formula (3):
wherein R
4
and R
5
are the same or different and are each a hydrogen atom or an arylmethyl group which may have a substituent, where at least one of R
4
and R
5
is an arylmethyl group which may have a substituent.
The present invention provides, in a further aspect, a process for producing a N-substituted-3-aminomethyltetrahydrofuran-2-one derivative. The process includes the step of deacetylating the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (1) by a reaction with a base to thereby yield a N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by following Formula (4):
wherein R
1
, R
2
, R
3
R
4
and R
5
have the same meanings as defined above.
In yet another aspect, the present invention provides a process for producing an 3-aminomethyltetrahydrofuran-2-one derivative. The process includes the steps of deacetylating the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (1) by a reaction with a base to thereby yield a N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (4), and subjecting this compound to hydrogenolysis to thereby yield an 3-aminomethyltetrahydrofuran-2-one derivative represented by following Formula (5):
wherein R
1
, R
2
and R
3
have the same meanings as defined above.
In another aspect, the present invention provides a process for producing an 3-acetyl-3-aminomethyltetrahydrofuran-2-one derivative. The process includes the step of subjecting the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (1) to hydrogenolysis to thereby yield an 3-acetyl-3-aminomethyltetrahydrofuran-2-one derivative represented by following Formula (6):
wherein R
1
, R
2
and R
3
have the same meanings as defined above.
Yet another aspect, the present invention provides a process for producing the 3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (5). The process includes the steps of subjecting the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (1) to hydrogenolysis to thereby yield the 3-acetyl-3-aminomethyltetrahydrofuran-2-one derivative represented by Formula (6), and deacetylating the resulting compound by a reaction with a base.
The present invention can easily yield novel 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivatives.
The present invention can easily yield N-substituted-3-aminomethyltetrahydrofuran-2-one derivatives and 3-acetyl-3-aminomethyltetrahydrofuran-2-one derivatives, which are useful for the preparation of the 3-aminomethyltetrahydrofuran-2-one derivatives.
In addition and advantageously, the present invention can efficiently yield 3-aminomethyltetrahydrofuran-2-one derivatives by a simple reaction.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
3-Acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one Derivatives and Production Thereof
In the 3-acetyl-N-substituted-3-aminomethyltetrahydrofuran-2-one derivatives represented by Formula (1), the substituents R
1
, R
2
and R
3
are the same or different and are each a hydrogen atom or an aliphatic hydrocarbon group.
Such aliphatic hydrocarbon groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl, pentyl, hexyl, decyl, dodecyl, andotheralkyl groups each having from about 1 to about 10, and preferably from about 1 to about 4, carbon atoms; vinyl, allyl, 1-butenyl, and other alkenyl groups each having from about 2 to about 10, and preferably from about 2 to about 4, carbon atoms; ethynyl, propynyl, and other alkynyl groups each having from about 2 to about 10, and preferably from about 2 to about 4, carbon atoms.
In Formula (1), the substituents R
4
and R
5
are the same or different and are each a hydrogen atom or an arylmethyl group which may have a substituent, where at least one of R
4
and R
5
is an arylmethyl group which may have a substituent. The substituent may be substituted on a carbon atom of whichever of the aryl moiety and the methyl moiety of the arylmethyl group. Such aryl groups include aromatic carbocyclic groups and aromatic heterocyclic groups.
Such aromatic carbocyclic groups include, but are not limited to, phenyl, naphthyl, and other aromatic carbocyclic groups each having from about 6 to about 20, and preferably from about 6 to about 10, carbon atoms. The aromatic heterocyclic groups include, for example, pyridyl group.
Substituents which may be substituted on the aryl moiety of the arylmethyl group include, but are not limited to, halogen atoms (e.g., fluorine, chlorine and bromine atoms), oxo group, hydroxyl group, substituted oxy groups (e.g., methoxy group and oth
Ikura Kiyoshi
Pan Li Rui
Tanaka Hiroki
Birch & Stewart Kolasch & Birch, LLP
Daicel Chemical Industries Ltd.
Owens Amelia
LandOfFree
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