74874-06-9Relevant academic research and scientific papers
Direct diastereoselective synthesis of (±)-cis- and (±)-trans-4-methylpipecolic acid and derivatives
Cossy, Janine,Belotti, Damien
, p. 2119 - 2120 (2007/10/03)
(±)-cis- or (±)-trans-4-Methylpipecolic acid and ester derivatives can be obtained directly by addition of electrophiles to α-lithiated N-Boc 4-methylpiperidine.
An Improved Synthesis of Homoproline and Derivatives
Shuman, Robert T.,Ornstein, Paul L.,Paschal, Jonathan W.,Gesellchen, Paul D.
, p. 738 - 741 (2007/10/02)
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 PtO2/H2 gives the homoprolines (5) in good yields as racemic cis isomers.This procedure also can be utilized for the preparation of 5,6-benzohomoprolines fromthe appropriate quinoline precursors.The N-tert-butyloxycarbonyl (Boc) derivatives of these amino acids (useful intermediates for peptide synthesis) were also prepared in good yields.
