Several synthetic pathways to the anticonvulsivum gabapentin (1‐(aminomethyl)cyclohexaneacetic acid) have been investigated. Advantages and drawbacks of the different routes are discussed, and the most economical and technically most feasible synthesis is pointed out.
SummaryComparison of PE. spectroscopic data for four series of enamines (including azetidine and some aziridine derivatives) for studying the influence of amine-ring size on electronic structure show the pyrrolidino group to exhibit the strongest amine/double bond coupling in sterically unconstrained enamines. However, the azetidino group accommodates best steric congestion due to dialkyl substitution at the /?-position of the enamine unit. Quantum-chemical calculations of equilibrium structures and energy profiles for amine rotations in model enamines by the PRDDO SCF method agree satisfactorily with experimental results. Notable exceptions are pyrrolidine derivatives for which PRDDO overestimates the amount of N-pyramidality.Recent experimental and theoretical work suggests that aliphatic enamines as well as vinylamine itself prefer non-planar equilibrium structures [ 1-31. In order to investigate the molecular and electronic structures of alkyl substituted enamines further, we have performed a photoelectron (PE.) spectroscopic study on simple alkyl substituted enamines as well as extended quantum-chemical structure calculations [4] [ 5 ] using the PRDDO SCF approximation [6]. We report here our results for the enamines listed in the Scheme. The series la-5a represents sterically unconstrained enamines that can be used to probe the influence of amine ring size on electronic structure. Comparison with lb-5b reveals the effect of steric con-0018-019X/81/8/2497-11$01.00/0 0 1981 Schweizerische Chemische Gesellschaft
Several synthetic pathways to the anticonvulsivum gabapentin (1 -(aminomethyl)cyclohexaneacetic acid) have been investigated. Advantages and drawbacks of the different routes are discussed, and the most economical and technically most feasible synthesis is pointed out.
the constant improvement of efficiency in project development and manufacturing is an essential issue for companies operating in the organic fine chemicals field. our strategy is based on the following concepts: (i) use of the whole high-technology portfolio available within the company, (ii) organisation of the process development in a process-oriented way, (iii) acceleration of the process transfer from laboratory to manufacturing scale by omitting intermediate piloting stages and (iv) maximisation of productivity by a flexible organisation of production units. how these concepts were implemented and which distribution of competencies within the r&D is needed, will be discussed in more detail in our contribution.
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