Optically active 1-phenyl-2-substituted propane derivatives and

Details Optically active 1-phenyl-2-substituted propane derivatives and Optically active 1-phenyl-2-substituted propane derivatives and

1994-06-02

1996-04-16

Chan, Nicky

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

Organic compounds

Sulfonate esters

549445, 549436, 549434, 549416, 558 44, 560254, 568652, 568651, 568649, C07C30973, C07C 43205, C07C 3908

Patent

active

055084613

ABSTRACT:
An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.

REFERENCES:
patent: 5061727 (1991-10-01), Bloom et al.
Reiner Luckenback, Beilsteins Handbook of Organic Chemistry, 1981, pp. 7403-7404.
Bloom, J., et al.; (R,R)-5-[2-[[2-(3-Chlorophenyl)-2-hydroxyethyl]-amino]propyl]-1,3-benzodio xole-2,2-dicarboxylate (CL 316,248), A Patent .beta.-Adrenergic Agonist Virtually Specific for .beta..sub.3 Receptors, A Promising Antidiabetic and Antiobesity Agency; J. Med. Chem., vol. 35, No. 16, pp. 3081-3084, (1992).
Conserva et al., Photochemistry, 29(1), 257-260 (1990).
Marques et al., ibid, 30(1), 360-361 (1992).

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