Method for resolving racemic compounds

Details Method for resolving racemic compounds Method for resolving racemic compounds

1995-03-02

1996-04-02

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31764

Patent

active

055042210

ABSTRACT:
A method for resolving racemic dimethyl-4,4'-dimethoxy-5,6,5',6'-di(methylenedioxy)biphenyl-2,2'-dicarbox ylate ("DDB"), in which a chiral .alpha.-alkyl benzyl alcohol is used as the resolving agent. More specifically, racemic DDB is first hydrolyzed to form dicarboxylic acid, which is then reacted with chiral .alpha.-alkyl benzyl alcohol to form two chiral isomers. The chiral isomers, after separation either by chromatography or by recrystalli-zation, are respectively hydrogenated and esterified to form chiral DDB isomers.

REFERENCES:
patent: 4996331 (1991-02-01), Kimura et al.
Nelson et al., "A Rapid Total Synthesis of an Ellagitannin", J. Org. Chem. 59:2577-2580, 1994.
Lipshutz et al., "Cyanocuprate-Mediated Intramolecular Biaryl Couplings Applied to an Ellagitannin, Synthesis of (+)-O-Permethyltellimagrandin II", Tetrahedron Letters vol. 35, No. 31, pp. 5567-5570, 1994.

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