Process for the production of optically active amino alcohols

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C564S462000

Reexamination Certificate

active

07038087

ABSTRACT:
An object of the present invention is to provide a process for the production of an optically active amino alcohol, particularly an optically active amino alcohol of a trans-form, being excellent in economy and efficiency, and suitable for industry using easily available and less expensive materials.The present invention relates to a process for the production of an optically active amino alcohol comprising the steps that an optically active hydroxy ester in a trans-form obtained by an asymmetric hydrogenation of an easily available β-keto ester is reacted with hydrazine, the resulting optically active hydrazinocarbonyl alcohol is subjected to a Curtius rearrangement in the presence of alcohol and protective group of amino group of the resulting optically active alkoxycarbonylamino alcohol is deprotected. As a result of the process for the production in accordance with the present invention, the objected substance is able to be prepared in a high optical purity and in a high yield.

REFERENCES:
patent: 61-063690 (1986-04-01), None
patent: 62-265293 (1987-11-01), None
patent: 04-139140 (1992-05-01), None
patent: 10-182678 (1998-07-01), None
patent: 11-269185 (1999-10-01), None
patent: 2000-016997 (2000-01-01), None
patent: WO 98/54350 (1998-12-01), None
Bertau et. al., Tetrahedron, Asymmetry, 12, (2001), 2103-2107.
Ratovelomanana, J. of Org. Chem., 567, (1998), 163-171).
M. Tichy et al.,Coll. Czechoslov. Chem. Commun., vol. 27, pp. 2907-2924, 1962.
E. Smissman et al.,J. Med. Chem., vol. 9, pp. 458-465, 1966.
M. Bertau et al.,Tetrahedron Asymmetry, vol. 12, No. 15, pp. 2103-2107, 2001.
V. Ratovelomanana et al.,Journal of Organ. Chem., vol. 567, pp. 163-171, 1998.
Priority Document No. 625679.
Mashima et al., “Synthesis of New Cationis BINAP-Ruthenium (II) Complexes and their Use in Asymmetric Hydrogenation[BINAP=2,2'-bis(diphenylphosphino)-1,1-binaphthyl]”, J. Chem. Soc., Chem. Commun, pp. 1208-1210, (1989).
Ami et al., “Lipase-catalyzed Kinetic Resolution of (+)—trans-and cis-2-Azidocycloalkanols”. Biosci. Biotechnol. Biochem., 63 (12), pp. 2150-2156, (1999).
Bertau et al., “A Novel Highly Stereoselective Synthesis of Chiral 5- and 4, 5-Substituted 2-Oxazolidinones”, Tetrahedron: Asymmetry 12 pp. 2103-2107, (2001).
Overman et al., “A Convenient Method for Obtaining trans-2-Aminocyclohexanol and trnas-2-Aminocyclopentanol in Enantiomerically Pure Form”, J. Org. Chem., vol. 50, pp. 4154-4155, (1985).
Coe et al., “Potassium trimethlsilanolate Induced Cleavage of 1,3-oxazolidin-2-and 5-ones, and Application to the Sysnthesis of ®-Salmeterol”, Org. Biomol. Chem, vol. 1, pp. 1106-1111, (2003).
Greene et al., “Protective Groups in Organic Sysnthesis”, Second Edition, pp. 314-341.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for the production of optically active amino alcohols 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 the production of optically active amino alcohols, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the production of optically active amino alcohols will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3555225

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.