GB839271A - 2-(hydroxyalkyl)-bicyclo[2,2,1]-heptene and -heptane derivatives and their preparation - Google Patents

2-(hydroxyalkyl)-bicyclo[2,2,1]-heptene and -heptane derivatives and their preparation

Info

Publication number
GB839271A
GB839271A GB5075/58A GB507558A GB839271A GB 839271 A GB839271 A GB 839271A GB 5075/58 A GB5075/58 A GB 5075/58A GB 507558 A GB507558 A GB 507558A GB 839271 A GB839271 A GB 839271A
Authority
GB
United Kingdom
Prior art keywords
reacting
bicyclo
preparation
hept
ene
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB5075/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Asta Medica GmbH
Original Assignee
Asta Werke AG Chemische Fabrik
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
Application filed by Asta Werke AG Chemische Fabrik filed Critical Asta Werke AG Chemische Fabrik
Publication of GB839271A publication Critical patent/GB839271A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0839271/IV (b)/1> (wherein R represents a straight or branched chain alkyl radical of 1-4 carbon atoms, X represents a hydrogen atom or a non-toxic salt-forming radical, and R1 represents -CH = CH-or -CH2-CH2-), and the preparation thereof by: (A) reacting 2-formyl-bicyclo-[2,2,1]-hept-5-ene with a Grignard compound R.Mg.Halogen, or (B) converting a 2-halobicyclo-[2,2,1]-hept-5-ene into its Grignard compound and reacting this with an aldehyde R-CHO, or (c) reducing a compound of the general formula <FORM:0839271/IV (b)/2> with aluminium isopropylate in isopropyl alcohol, and in each case, if desired, catalytically hydrogenating the product to convert -CH= CH- to -CH2-CH2-, or (D) reducing the starting materials of (A), (B) or (C) to the corresponding ring-saturated compounds and subjecting these to processes (A), (B) or (C); and in all cases reacting the resulting carbinols with succinic anhydride to form their succinic acid hemi-esters and, if desired, dissolving these in an aqueous solution of a salt-forming base. The products are useful therapeutically on account of the cholalogue activity.
GB5075/58A 1957-02-23 1958-02-17 2-(hydroxyalkyl)-bicyclo[2,2,1]-heptene and -heptane derivatives and their preparation Expired GB839271A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE839271X 1957-02-23

Publications (1)

Publication Number Publication Date
GB839271A true GB839271A (en) 1960-06-29

Family

ID=6761889

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5075/58A Expired GB839271A (en) 1957-02-23 1958-02-17 2-(hydroxyalkyl)-bicyclo[2,2,1]-heptene and -heptane derivatives and their preparation

Country Status (1)

Country Link
GB (1) GB839271A (en)

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