61212-32-6Relevant articles and documents
Phase behavior and crystal structure of 3-(1-naphthyloxy)- and 3-(4-indolyloxy)-propane-1,2-diol, synthetic precursors of chiral drugs propranolol and pindolol
Bredikhin, Alexander A.,Gubaidullin, Aidar T.,Bredikhina, Zemfira A.,Fayzullin, Robert R.,Samigullina, Aida I.,Zakharychev, Dmitry V.
, p. 104 - 111 (2013)
Valuable precursors of popular chiral drugs propranolol and pindolol, 3-(1-naphthyloxy)-propane-1,2-diol 3 and 3-(4-indolyloxy)-propane-1,2-diol 4 were investigated by IR spectroscopy, DSC, and X-ray diffraction methods. Both compounds, crystallizing from enantiopure feed material, form "guaifenesin-like" crystal packing in which the classic H-bonded bilayers, framed in both sides by hydrophobic fragments of the molecules, acts as the basic crystal-forming motif. Diol 4 prone to spontaneous resolution and conserves its packing pattern crystallizing from racemate. Under the same conditions, diol 3 forms weakly stable solid racemic compound. Some reasons for such a behavior are identified and discussed.
Syntheses of (S)-(-)-Pindolol and -(R)-(-)-Pindolol Utilizing a Lanthanum-Lithium-(R)-BINOL ((R)-LLB) Catalyzed Nitroaldol Reaction
Sasai, Hiroaki,Yamada, Yoichi M. A.,Suzuki, Takeyuki,Shibasaki, Masakatsu
, p. 12313 - 12318 (2007/10/02)
An efficient synthesis of (-)-pindolol, an effective β-blocker, has been achieved utilizing a lanthanum-lithium-(R)-BINOL ((R)-LLB) catalyzed nitroaldol reaction as a key step.This methodology was applicable to a synthesis of (13)C-labeled (-)-pindolol, which would be useful as a biological tool for tracing the metabolism of β-blocker and 5-HT1A receptor antagonist.The mechanistic aspects of the LLB catalyzed nitroaldol reaction are also discussed.
