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Figure 4: Overview over aryloxy vicinyl amino alcohols produced
by continuous synthesis.
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Described is the development of a convergent chemical assembly
system consisting of four modules that reliably produces aryl and
aryloxy β-amino alcohols in good yields. Modular flow units
include biphasic oxidations,5 Corey-Chaykovsky epoxidations,
aryloxy alkylations, and epoxide aminolysis.12 Aqueous in-line
workup using liquid-liquid extractors resulted in continuous
processes without intermediate purification. Starting from phenols
or benzyl alcohols five active pharmaceutical ingredients for the
treatment of hypertension, agina pectoris, and bronchiodilation were
produced. Enantiopure aryloxy β-amino alcohols can be prepared by
starting from R/S epichlorohydrin.
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M. W. Bedore, N. Zaborenko, K. F. Jensen, T. F. Jamison, Org. Process
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† These authors contributed equally to this work.
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Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1,
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For the use of CsF as catalyst, see: K. Kitaori, Y. Furukawa, H.
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This yield compares favourably with a comparable two-step batch process
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