Process for preparing an optically active phenylglycidyl acid de

Details Process for preparing an optically active phenylglycidyl acid de Process for preparing an optically active phenylglycidyl acid de

1998-02-23

2000-02-15

Richter, Johann

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549549, C07D30108, C07D30338

Patent

active

060255064

ABSTRACT:
The invention relates to a process for preparing an optically active trans-compound having formula (1), in which R represents a phenyl group, whether or not substituted, preferably p-methoxyphenyl, and A is derived from an optically active compound, in which an aldehyde having formula (2), in which R is as defined above, is, in the presence of a base, brought into contact with an optically active acetyl compound having formula (3), in which X represents a leaving group and in which A is derived from an amino alcohol, preferably a .beta.-amino alcohol having a rigid structure.
Particularly good results were obtained when use was made of a compound having formula (3), in which A is derived from an amino indanol compound having formula (4), in which R.sub.1 and R.sub.2 represent a (hetero)alkyl or (hetero)aryl group, whether or not substituted, having 1-10 C atoms, or R.sub.1 and R.sub.2 constitute an aromatic or aliphatic ring together with the N atom to which they are bound, in particular in which R.sub.1 and R.sub.2 each independently of one another represent methyl, ethyl, isopropyl, n-propyl, n-butyl, allyl, benzyl or tosyl.

REFERENCES:
patent: 5008433 (1991-04-01), Palmer
Schwartz et al., Enantioselective Synthesis of Calcium Channel Blockers of the Diltiazem Group. J. of Org. Chem. 57(3) 1992, pp. 851-856.

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