Process for producing optically active amines

Details Process for producing optically active amines Process for producing optically active amines

1991-10-07

1993-04-06

Raymond, Richard L.

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

Organic compounds

Amino nitrogen containing

546329, 558354, 558422, 564302, 564303, 564304, 564321, 564374, 564375, 564382, 564384, 564385, 564389, 564415, 564428, 564429, 564463, 564489, C07C20988, C07C20940

Patent

active

052005615

ABSTRACT:
Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.6 denotes an alkyl group, aralkyl group or alkyl-substituted silyl group, and R.sub.7 and R.sub.8 are as defined above.
The optically active amine obtained can be used as a resolving agent for preparing medicinal agents, agricultural chemicals, or intermediates thereof.

REFERENCES:
Tetrahedron Letters, vol. 29, No. 2, pp. 223-224, 1988, "Asymmetric Reduction of Oxime Ethers, Distinction of Anti and Syn Isomers Leading to Enantiomeric Amines", Sakito et al.
J. Chem. Soc., Perkins Trans. 1, 1985, pp. 2039-2044, Itsuno et al., "Asymmetric Synthesis Using Chirally Modified Borohydrides. Part 3. Enantioselective Reduction of Ketones and Oxime Ethers with Reagents Prepared from Borane and Chiral Amino Alcohols".
Sakito et al. "Asymmetric Reduction, etc." vol. 29, No. 2, pp. 223-224 (1988).
Itsuno et al., "Asymmetric Synthesis using Ketones and Oxime Ethers, etc." J. Chem Soc. Perkins Trans. 1, 1985 pp. 2039-2044.
March Advanced Organic Chemistry, 3rd Ed, John Wiley and Sons New York, 1985, pp. 702-703.

Affiliated with

Also associated with

Rating

Process for producing optically active amines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing optically active amines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing optically active amines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-538075