Octahydro-1H-pyrrolo[2, 3-c]pyridine derivative, octahydro-1H-pyrrolo[3, 2-c]pyridine derivative and preparation methods thereof

Abstract

The invention provides an octahydro-1H-pyrrolo[2, 3-c]pyridine derivative shown as formula (I), an octahydro-1H-pyrrolo[3, 2-c]pyridine derivative shown as formula (II) and preparation methods thereof. Specifically, R1 is hydrogen, alkyl of C1-C9, benzyl, or R4C(O)-, R4 is alkyl of C1-C9, R5O-, aryl, benzyl or substituted benzyl, R5 is alkyl of C1-C9, aryl, benzyl or substituted benzyl; R2 is hydrogen, alkyl of C1-C9, benzyl or R6C(O)-, R6 is alkyl of C1-C9, R7O-, aryl, benzyl or substituted benzyl, R7 is alkyl of C1-C9, aryl, benzyl or substituted benzyl, R3 is COOR8, and R8 is hydrogen, alkyl of C1-C9, benzyl or substituted benzyl. The preparation method is novel, and especially realizes the efficient conversion process from the cyano group to a pyrrolidine structure in one step. The raw materials and ragenets are easily available and cheap, the reaction conditions are mild, the operation is simple, and the generated octahydro-1H-pyrrolo[2, 3-c]pyridine derivative and the octahydro-1H-pyrrolo[3, 2-c]pyridine derivative, especially derivatives with carboxyl or ester, can be used as an important intermediate of new drug research and development due to a rigid-cyclo structure of a trifunctional group. (formula (I) and formula (II)).

Description

technical field [0001] The invention relates to the field of chemical technology, in particular to octahydro-1H-pyrrolo[2,3-c]pyridine derivatives and octahydro-1H-pyrrolo[3,2-c]pyridine derivatives and preparation methods thereof. Background technique [0002] Heterocyclic compounds are by far the largest classical branch of organic chemicals and play an extremely important role in the fields of biopharmaceuticals and chemical industry. In particular, nitrogen-containing heterocyclic compounds have a wide range of biological activities and occupy an extremely important position in various fields such as medicine, pesticides and life sciences. The synthesis of these compounds has always been a research hotspot in the field of organic synthesis. [0003] In addition to its inherent ability to bind to the target, the nitrogen-containing heterocyclic compound is the potential active center of these drugs, and has biological activity. It is also reflected in the ability of the s...

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Problems solved by technology

[0025] All the above-mentioned methods only report the preparation of unsubstituted octahydropyrrolo[2,3-c]pyridine or octahydropyrrolo[3,2-c]pyridine, and it is difficult to introduce other functional groups into the structure, especially in this paper. In the structure of the compound described in the invention, a carboxyl or ester group is introduced on the angular carbon atom, so there are great limitations in structural modification and diversification of the compound structure

At the same time, there are also problems such as expensive starting materials or tedious synthetic routes.

Both method 1 and method 2 use 5- or 6-azaindole derivatives as starting raw materials, which are not easy to obtain on the market and are relatively expensive, so the cost is higher

The preparation routes of methods 3, 4 and 5 are long, and the conditions are harsh and even microwave means are used, so it is not suitable for large-scale production

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