Stereopreferential synthesis of 3-(1-phenylprop-2-yl)-5-phenylox

Details Stereopreferential synthesis of 3-(1-phenylprop-2-yl)-5-phenylox Stereopreferential synthesis of 3-(1-phenylprop-2-yl)-5-phenylox

1994-05-03

1995-11-21

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D26320

Patent

active

054688655

ABSTRACT:
The (R,R)-diastereoisomer of oxazolidin-2-ones, which are chemical intermediates for the preparation therapeutic agents useful in the treatment of diabetes and hyperglycemia, are prepared substantially free of isomeric forms through reduction of an acid addition salt of an (R)-N-protected-N-phenylcarboxymethyl-1-phenylprop-2-ylamine to form a secondary alcohol of predominantly the (R,R) chiral form in preference to others, removal of the protecting group to form a secondary amine, and allowing the secondary amine to react with a source of carbonyl groups. A typical embodiment involves the preparation of (R,R)-3-[1-(3,4-dimethoxyphenyl)prop-2-yl]-5-(3-chlorophenyl)oxazolidin-2- one in which both the chemical purity and optical purity are in excess of 99%.

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