Abstract
An efficient three-step methodology developed for the preparation of 1,2-amino alcohols. In the first step a rapid coupling between bromoketones and potassium phthalimide in ionic liquid produced α-phthalimido ketones in quantitative yields, which is followed by a facile reduction using NaCNBH3 in acetic acid to give corresponding phthalimido alcohols and finally effecting hydrazinolysis in water at 60 °C to yield biologically important 1,2-amino alcohols.
GRAPHICAL ABSTRACT
ACKNOWLEDGMENT
One of the authors (A. R.) is thankful to the Council of Scientific and Industrial Research, New Delhi, India, for the award of a junior research fellowship.
Notes
Notes. Phth, phthalimide; T (min), time in minutes; Y (%), isolated yield in %.
Notes. Phth, phthalimide; T (h), time in hours; Y (%), isolated yield in %; ND, not detected. The structures of the products were established from their spectral (1H, 13C NMR, and MS) and analytical data.
a anti/syn = > 99 (using NMR).
b anti/syn = 43:57.
c anti/syn = 1:1.
2-eq. of hydrazine hydrate was used and yield mentioned was isolated yield; structures of the final products were confirmed by spectroscopic analysis.