US 5,508,461 A · Optically active 1-phenyl-2-substituted propane derivatives and methods of producing the same

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.

Claims8

Dependent claims

An (S)-1-phenyl-2-substituted propane derivative shown by the following formula ##STR12## wherein R.sup.1 and R.sup.2 represent (a) the same or different, a hydrogen atom or a protective group for hydroxyl group, or

(b) R.sup.1 and R.sup.2 may form a 5- to 10-membered ring with the adjacent oxygen atoms;
R.sup.3, R.sup.4 and R.sup.5 independently represent a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a nitro group or a halogen atom;
and
X represents (i) a hydroxyl group or hydroxyl group protected with a protective group,
(ii) an alkylsulfonyloxy group which may be substituted with a halogen atom,
(iii) an arylsulfonyloxy group which may be substituted with a substituent selected from the group consisting of a nitro group, a halogen atom and a C.sub.1-4 alkyl group, or
(iv) a halogen atom.

4 more elements

An (R)-1-phenyl-2-substituted propane derivative shown by the following formula ##STR15## wherein (a) R.sup.1 and R.sup.2 are the same or different and represents a hydrogen atom or a protective group for a hydroxyl group, or (b) R.sup.1 and R.sup.2 may form a 5- to 10-membered ring with the adjacent oxygen atoms;

R.sup.3, R.sup.4 and R.sup.5 independently represent a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a nitro group of a halogen atom;
and
X represents (i) a hydroxyl group or a hydroxyl group protected with a protective group, (ii) an alkylsulfonyloxy group which may be substituted with a halogen atom, (iii) an arylsulfonyloxy group which may be substituted with a substituent selected from the group consisting of a nitro group, a halogen atom and a C.sub.1-4 alkyl group, or (iv) a halogen atom.

Dependencies are inferred from the claim text.

Optically active 1-phenyl-2-substituted propane derivatives and methods of producing the same

Life of this patent

Optically active 1-phenyl-2-substituted propane derivatives and methods of producing the same

Life of this patent

Abstract

Claims8