GB1108978A - A process for the preparation of tetrahydro-indane derivatives and certain novel tetrahydro-indane derivatives perse - Google Patents

A process for the preparation of tetrahydro-indane derivatives and certain novel tetrahydro-indane derivatives perse

Info

Publication number
GB1108978A
GB1108978A GB43189/67A GB4318967A GB1108978A GB 1108978 A GB1108978 A GB 1108978A GB 43189/67 A GB43189/67 A GB 43189/67A GB 4318967 A GB4318967 A GB 4318967A GB 1108978 A GB1108978 A GB 1108978A
Authority
GB
United Kingdom
Prior art keywords
methylene
prepared
ethyl
tetrahydro
benzoyl
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
GB43189/67A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1108978A publication Critical patent/GB1108978A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes

Abstract

Compounds of the formula <FORM:1108978/C2/1> (wherein R1 is lower, i.e. C1- 6, alkyl; Z1 is CO or CH(OR20), R20 being H, lower alkyl, lower alkoxy-lower alkyl, phenyl-lower alkyl, tetrahydropyranyl, lower alkanoyl, benzoyl, nitro-benzoyl, carboxy-lower alkanoyl, carboxy-benzoyl, trifluoro-acetyl or camphorsulphonyl; and T is -CX=CH-, -C(OR3)=CH- or -Q-CH2-, X being Cl, Br or I, R3 being lower alkyl, and Q being carbonyl, lower alkylenedioxy-methylene, di-lower alkoxy-methylene, hydroxy-methylene, tetrahydropyranyloxy-methylene or phenyl-lower alkoxy-methylene) and optical antipodes and racemates thereof, all of which except 1-[1-keto-7ab - methyl - 5 - oxo - 5,6,7,7a - tetrahydroindanyl - (4)] - butanone - (3) are novel, are prepared by treating the corresponding 4-unsubstituted - tetrahydroindanones with a compound [H or R1]-CH2-V wherein V is -CO-CH = CH2, -CX = CH-CH2-X1, -C(OR3) = CH-CH2-X1 or -Q-CH2-CH2-X1, X1 being Cl, Br, I, tosyloxy or mesyloxy in the presence of a base. Resolved starting materials can be used or the products can be resolved by known methods. Alkyleneketal products can be hydrolysed to the free ones. 1b - tetrahydropyranyloxy - 7ab - methyl - 5 - oxo - 5,6,7,7a - tetrahydroindane is prepared from the 1b -ol and dihydropyran, the 1b -ol being previously resolved via the brucine salt of its hydrogen phthalate. The t -butyl ether of the 1b -ol is prepared from the ol and isobutylene, and the corresponding ethoxy-ethyl ether from the ol and ethyl vinyl ether. 1-Iodo-pentanone-(3) is prepared by heating 2 - (2 - chloro - ethyl) - 2 - ethyl - 1,3 - dioxolane with sodium iodide in acetone.
GB43189/67A 1965-10-13 1966-10-11 A process for the preparation of tetrahydro-indane derivatives and certain novel tetrahydro-indane derivatives perse Expired GB1108978A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US49567265A 1965-10-13 1965-10-13
US54467766A 1966-04-25 1966-04-25

Publications (1)

Publication Number Publication Date
GB1108978A true GB1108978A (en) 1968-04-10

Family

ID=27051843

Family Applications (4)

Application Number Title Priority Date Filing Date
GB43189/67A Expired GB1108978A (en) 1965-10-13 1966-10-11 A process for the preparation of tetrahydro-indane derivatives and certain novel tetrahydro-indane derivatives perse
GB43190/67A Expired GB1108979A (en) 1965-10-13 1966-10-11 Novel hexahydro-idane derivatives
GB45453/66A Expired GB1108976A (en) 1965-10-13 1966-10-11 A process for the manufacture of benz[e]idenes
GB43188/67A Expired GB1108977A (en) 1965-10-13 1966-10-11 Novel pentanone derivatives

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB43190/67A Expired GB1108979A (en) 1965-10-13 1966-10-11 Novel hexahydro-idane derivatives
GB45453/66A Expired GB1108976A (en) 1965-10-13 1966-10-11 A process for the manufacture of benz[e]idenes
GB43188/67A Expired GB1108977A (en) 1965-10-13 1966-10-11 Novel pentanone derivatives

Country Status (11)

Country Link
JP (1) JPS5017471B1 (en)
AT (1) AT278767B (en)
BE (1) BE687996A (en)
BR (1) BR6683552D0 (en)
CH (2) CH525851A (en)
ES (1) ES332168A1 (en)
FR (1) FR1510878A (en)
GB (4) GB1108978A (en)
IL (1) IL26592A (en)
NL (1) NL6614414A (en)
SE (1) SE331092B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3975440A (en) * 1970-01-21 1976-08-17 Hoffmann-La Roche Inc. Asymmetric synthesis of organic compounds
CN114345366B (en) * 2022-01-14 2023-05-30 万华化学集团股份有限公司 Preparation method of 3-methoxy-4-hydroxymandelic acid oxidation catalyst

Also Published As

Publication number Publication date
DE1568792A1 (en) 1970-07-09
IL26592A (en) 1970-12-24
CH525851A (en) 1972-07-31
NL6614414A (en) 1967-04-14
FR1510878A (en) 1968-01-26
BE687996A (en) 1967-04-10
GB1108977A (en) 1968-04-10
SE331092B (en) 1970-12-14
DE1568792B2 (en) 1975-10-09
BR6683552D0 (en) 1973-12-04
GB1108976A (en) 1968-04-10
JPS5017471B1 (en) 1975-06-20
ES332168A1 (en) 1967-07-16
GB1108979A (en) 1968-04-10
AT278767B (en) 1970-02-10
CH530360A (en) 1972-11-15

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