An improved synthesis of homoproline and derivatives

…, PL Ornstein, JW Paschal, PD Gesellchen

Index: Shuman, Robert T.; Ornstein, Paul L.; Paschal, Jonathan W.; Gesellchen, Paul D. Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 738 - 741

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Citation Number: 78

Abstract

An improved, general synthesis of substituted homoprolines has been developed by using readily available substituted pyridines (1). A key step in this synthetic procedure involves the known conversion of pyridine N-oxides to 2-cyanopyridines (3) in nearly quantitative yields. The resulting nitriles are hydrolyzed to the corresponding pyridine-2-carboxylic acids (4). Subsequent reduction of the aromatic ring with Pt02/H2 gives the homoprolines (5) in ...