Title:
CHIRAL AMINO ALCOHOLS AND PROCESS FOR PREPARATION OF SAME
Document Type and Number:
WIPO Patent Application WO2002022550
Kind Code:
A3
Abstract:
The disclosed invention comprises a compound having the formula (I), in which R<1> and R<2> independently represent a hydrogen or an alkyl group of 4 carbon atoms or greater. Further disclosed is a process for the preparation of the disclosed chiral amino alcohols from a starting amine compound and a limonene oxide.
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Inventors:
BAKTHAN SINGARAM (US)
WILLIAM CHRISMAN (US)
GORALSKI CHRISTIAN T
WILLIAM CHRISMAN (US)
GORALSKI CHRISTIAN T
Application Number:
PCT/US2001/027262
Publication Date:
September 12, 2003
Filing Date:
August 30, 2001
Export Citation:
Assignee:
DOW CHEMICAL CO (US)
BAKTHAN SINGARAM (US)
WILLIAM CHRISMAN (US)
BAKTHAN SINGARAM (US)
WILLIAM CHRISMAN (US)
International Classes:
C07C213/04; C07C215/44; C07D209/44; C07D211/14; C07D211/62; C07D217/04; C07D233/61; C07D295/096; C07D295/205; C07D521/00; (IPC1-7): C07C215/44; C07C213/04; C07D211/62; C07D217/26; C07D233/61; C07D295/08; C07D295/20
Domestic Patent References:
| WO2001070707A2 | 2001-09-27 |
Other References:
CHRISMAN W ET AL: "A simple and convenient synthesis of beta-amino alcohol chiral auxiliaries based on limonene oxide", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 42, no. 34, 20 August 2001 (2001-08-20), pages 5805 - 5807, XP004295929, ISSN: 0040-4039
NEWHALL W F ET AL: "DERIVATIVES OF (+)-LIMONENE: QUATERNARY AMMONIUM COMPOUNDS THAT RETARD PLANT GROWTH", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 14, no. 1, January 1966 (1966-01-01), pages 23 - 27, XP001073672, ISSN: 0021-8561
CHEMICAL ABSTRACTS, vol. 88, no. 25, 19 June 1978, Columbus, Ohio, US; abstract no. 191084, KOZHIN, S. A. ET AL: "Products of the aminolysis of limonene 1,2-monoxide" XP002247264
HO T-L ET AL: "A New Synthesis of (-)-Furodysin", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 36, no. 6, 6 February 1995 (1995-02-06), pages 947 - 948, XP004028714, ISSN: 0040-4039
BAKER R ET AL: "IDENTIFICATION AND SYNTHESIS OF (Z)-(1'S,3'R,4'S)(-)-2-(3',4-EPOXY-4' -METHYLCYCLOHEXYL)-6-METHYLHEPTA-2,5-DIENE, THE SEX PHEROMONE OF THE SOUTHERN GREEN STINKBUG, NEZARA VIRIDULA (L.)", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 6, 1987, pages 414 - 416, XP001073786, ISSN: 0022-4936
KUCZYNSKI H ET AL: "UEBER EINEN STEREOSPEZIFISCHEN WEG ZUR DARSTELLUNG DER ALPHA,BETA-UNGESAETTIGTEN ALKOHOLE", BULLETIN DE L'ACADEMIE POLONAISE DE SCIENCES. SERIE DES SCIENCES CHIMIQUES, WARSZAW, PL, vol. 9, no. 9, 1961, pages 551 - 554, XP008003779, ISSN: 0001-4095
TEULON J-M ET AL: "SUR L'OUVERTURE DES EPXYDES DU LIMONENE", COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L'ACADEMIE DES SCIENCES, SERIE C: SCIENCES CHIMIQUES, GAUTHIER-VILLARS. MONTREUIL, FR, vol. 262, no. 12, 21 March 1966 (1966-03-21), pages 1021 - 1024, XP001073670
NEWHALL, WILLIAM F.: "Derivatives of (+)-limonene. III. A stereospecific synthesis of cis- and trans-p-menth-8-ene 1,2-epoxides", JOURNAL OF ORGANIC CHEMISTRY (1964), 29(1), 185-7, 1964, XP002247263
NEWHALL W F ET AL: "DERIVATIVES OF (+)-LIMONENE: QUATERNARY AMMONIUM COMPOUNDS THAT RETARD PLANT GROWTH", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 14, no. 1, January 1966 (1966-01-01), pages 23 - 27, XP001073672, ISSN: 0021-8561
CHEMICAL ABSTRACTS, vol. 88, no. 25, 19 June 1978, Columbus, Ohio, US; abstract no. 191084, KOZHIN, S. A. ET AL: "Products of the aminolysis of limonene 1,2-monoxide" XP002247264
HO T-L ET AL: "A New Synthesis of (-)-Furodysin", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 36, no. 6, 6 February 1995 (1995-02-06), pages 947 - 948, XP004028714, ISSN: 0040-4039
BAKER R ET AL: "IDENTIFICATION AND SYNTHESIS OF (Z)-(1'S,3'R,4'S)(-)-2-(3',4-EPOXY-4' -METHYLCYCLOHEXYL)-6-METHYLHEPTA-2,5-DIENE, THE SEX PHEROMONE OF THE SOUTHERN GREEN STINKBUG, NEZARA VIRIDULA (L.)", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, CHEMICAL SOCIETY. LETCHWORTH, GB, no. 6, 1987, pages 414 - 416, XP001073786, ISSN: 0022-4936
KUCZYNSKI H ET AL: "UEBER EINEN STEREOSPEZIFISCHEN WEG ZUR DARSTELLUNG DER ALPHA,BETA-UNGESAETTIGTEN ALKOHOLE", BULLETIN DE L'ACADEMIE POLONAISE DE SCIENCES. SERIE DES SCIENCES CHIMIQUES, WARSZAW, PL, vol. 9, no. 9, 1961, pages 551 - 554, XP008003779, ISSN: 0001-4095
TEULON J-M ET AL: "SUR L'OUVERTURE DES EPXYDES DU LIMONENE", COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L'ACADEMIE DES SCIENCES, SERIE C: SCIENCES CHIMIQUES, GAUTHIER-VILLARS. MONTREUIL, FR, vol. 262, no. 12, 21 March 1966 (1966-03-21), pages 1021 - 1024, XP001073670
NEWHALL, WILLIAM F.: "Derivatives of (+)-limonene. III. A stereospecific synthesis of cis- and trans-p-menth-8-ene 1,2-epoxides", JOURNAL OF ORGANIC CHEMISTRY (1964), 29(1), 185-7, 1964, XP002247263
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