WO1991002711A3 - 7,7-dimethylnorbornane derivatives - Google Patents

7,7-dimethylnorbornane derivatives Download PDF

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Publication number
WO1991002711A3
WO1991002711A3 PCT/US1990/004722 US9004722W WO9102711A3 WO 1991002711 A3 WO1991002711 A3 WO 1991002711A3 US 9004722 W US9004722 W US 9004722W WO 9102711 A3 WO9102711 A3 WO 9102711A3
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WO
WIPO (PCT)
Prior art keywords
dimethylnorbornyl
exo
alanine
making
disclosed
Prior art date
Application number
PCT/US1990/004722
Other languages
French (fr)
Other versions
WO1991002711A2 (en
Inventor
Yoshifumi Yuasa
Ako Tachikawa
Yoshiki Oketa
Toru Watanabe
Akira Nagakura
Jamges G Sweeny
Georga A King Iii
Original Assignee
Coca Cola Co
Takasago Perfumery Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP1213116A external-priority patent/JPH0383936A/en
Application filed by Coca Cola Co, Takasago Perfumery Co Ltd filed Critical Coca Cola Co
Priority to BR909007609A priority Critical patent/BR9007609A/en
Publication of WO1991002711A2 publication Critical patent/WO1991002711A2/en
Publication of WO1991002711A3 publication Critical patent/WO1991002711A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/20—Vanadium, niobium or tantalum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/053—Sulfates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/105—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings
    • C07C47/115—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing rings containing condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Biophysics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention discloses 7,7-dimethylnorbor- nane derivatives useful as intermediates for the production of various synthetic perfumes and high intensity sweeteners. 2R-exo-7,7-Dimethylnorbornyl acetaldehyde, 3-(2R-exo-7,7-dimethylnorbornyl)-2-amino- propionitrile,3-(2R-exo-7,7-dimethylnorbornyl)alanine hydantoin and N-acyl-3-(2R-exo-7,7-dimethylnorbornyl) alanines are disclosed. The present invention describes a process for making 7,7-dimethylnorbornane derivatives, 3-(2R-exo-7,7-dimethylnorbornyl)-L-alanine lower alkyl esters and alpha-L-aspartyl-3-(2R-exo-7,7-dimethylnorbornyl)-L-alanine lower alkyl esters. A process for making alpha-fenchene, a process for making alpha-fenchyl alcohol and a process for making an optically active 3-(2R-exo-7,7-dimethylnorbornyl)-L-alanine or its lower alkyl ester are also disclosed. Dehydration and rearrangement catalysts are also disclosed.
PCT/US1990/004722 1989-08-21 1990-08-20 7,7-dimethylnorbornane derivatives WO1991002711A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BR909007609A BR9007609A (en) 1989-08-21 1990-08-20 COMPOUND, PHENCHYL ALCOHOL DEHYDRATION CATALYST, AND PROCESSES TO PRODUCE THE INTERIOR ALKYLIC STERIS OF 3- (2R-EXO-7,7-DIMETHYL-NORBORNANO) -L-ALANINE, AND ALFA-L-ASPARTIL- (2R-EXO -7,7-DIMETHYLNORBORNIL) -L-ALANINE, TO PURIFY ALCOHOL (+) - ALFA-FENCHILICO, TO PRODUCE ALFA-FENCHENO, AND TO PRODUCE A 3- (2R-EXO-7,7-DIMETHILNORBORNIL) -L- OPTICALLY ACTIVE ALANINE OR ITS INTERIOR ALKYLIC ESTER

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US39658689A 1989-08-21 1989-08-21
JP1213116A JPH0383936A (en) 1989-08-21 1989-08-21 7, 7-dimethylnorvolnane derivative
US396,586 1989-08-21
JP64/2131116 1989-08-21

Publications (2)

Publication Number Publication Date
WO1991002711A2 WO1991002711A2 (en) 1991-03-07
WO1991002711A3 true WO1991002711A3 (en) 1991-05-02

Family

ID=26519616

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/004722 WO1991002711A2 (en) 1989-08-21 1990-08-20 7,7-dimethylnorbornane derivatives

Country Status (4)

Country Link
AU (1) AU6293790A (en)
BR (1) BR9007609A (en)
CA (1) CA2065014A1 (en)
WO (1) WO1991002711A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6740406B2 (en) * 2000-12-15 2004-05-25 Kimberly-Clark Worldwide, Inc. Coated activated carbon

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0284084A2 (en) * 1987-03-27 1988-09-28 The Coca-Cola Company Intensely sweet L-aspartyl-3-(Bicycloalkyl)-L-alanine alkyl esters

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0284084A2 (en) * 1987-03-27 1988-09-28 The Coca-Cola Company Intensely sweet L-aspartyl-3-(Bicycloalkyl)-L-alanine alkyl esters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, volume 91, no. 19, 5 November 1979, (Columbus, Ohio, US), Y. Matsubara et al.: "Studies on hydration of terpenes. 15. Syntheses of exo- and endo-isofenchol", see page 656 *

Also Published As

Publication number Publication date
CA2065014A1 (en) 1991-02-22
BR9007609A (en) 1992-08-18
WO1991002711A2 (en) 1991-03-07
AU6293790A (en) 1991-04-03

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