GB605444A - Improvements in or relating to the resolution of racemic ª‡-hydroxy-ª‰-ª‰-dimethyl-ª†-butyrolactone - Google Patents

Improvements in or relating to the resolution of racemic ª‡-hydroxy-ª‰-ª‰-dimethyl-ª†-butyrolactone

Info

Publication number
GB605444A
GB605444A GB20787/44A GB2078744A GB605444A GB 605444 A GB605444 A GB 605444A GB 20787/44 A GB20787/44 A GB 20787/44A GB 2078744 A GB2078744 A GB 2078744A GB 605444 A GB605444 A GB 605444A
Authority
GB
United Kingdom
Prior art keywords
lactone
complex
brucine
racemic
aqueous solution
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
GB20787/44A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB605444A publication Critical patent/GB605444A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

Landscapes

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

Abstract

Racemic a -hydroxy-b : b -dimethyl-g -butyrolactone is resolved by reacting the racemic lactone with brucine alkaloid in a neutral aqueous or inert organic solvent in which the brucine-laevolactone complex thus formed is insoluble, or alternatively, in an inert organic solvent in which said complex is soluble and in this case precipitating the complex by the addition of a miscible liquid which is a non-solvent for the complex, separating said complex and recovering the laevo-rotatory lactone therefrom; the lactone may be recovered by treating the complex with an aqueous solution of a base, extracting the liberated brucine with chloroform or ethylene dichloride and isolating the #i-lactone from the residual aqueous solution or by treating the complex with an acid and extracting the #i-lactone with ether or benzene. In examples: (1) an ethanol solution of brucine base and an acetone solution of racemic lactone are mixed and cooled and the resulting crystalline brucine-#i-lactone complex removed; (2) an aqueous solution of brucine sulphate is neutralized with sodium hydroxide and the racemic lactone added with stirring and the resulting precipitated #i-lactone complex removed; (3) brucine base is dissolved in hot ethyl acetate or dioxane, the racemic lactone added and after cooling, the precipitated #i-lactone brucine complex is filtered off; chloroform may be used in place of ethyl acetate, the required #i-lactone complex being precipitated by adding ether. In each case, the #i-lactone is recovered from the complex by one of the methods described above. The properties of the complex are compared with those of a true brucine salt of the corresponding butyric acid prepared, for example, by reacting an aqueous solution of the barium salt derived from the #i-lactone, with brucine sulphate.
GB20787/44A 1943-11-27 1944-10-25 Improvements in or relating to the resolution of racemic ª‡-hydroxy-ª‰-ª‰-dimethyl-ª†-butyrolactone Expired GB605444A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US605444XA 1943-11-27 1943-11-27

Publications (1)

Publication Number Publication Date
GB605444A true GB605444A (en) 1948-07-23

Family

ID=22030164

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20787/44A Expired GB605444A (en) 1943-11-27 1944-10-25 Improvements in or relating to the resolution of racemic ª‡-hydroxy-ª‰-ª‰-dimethyl-ª†-butyrolactone

Country Status (1)

Country Link
GB (1) GB605444A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1033652B (en) * 1954-09-09 1958-07-10 Upjohn Co Process for the resolution of racemic ª ‡ -oxy-ª ‰, ª ‰ -dimethyl-ª † -butyrolactone into its d (-) - and 1 (+) - stereomers
US2967869A (en) * 1958-06-19 1961-01-10 Nopco Chem Co Process for obtaining d(-)-alpha-hydroxy-beta, beta-dimethyl-gamma-butyrolactone
US3009922A (en) * 1958-06-19 1961-11-21 Nopco Chem Co Process for obtaining d(-)-alpha-hydroxy-beta, beta-dimethyl-gamma-butyrolactone
US3150175A (en) * 1961-08-28 1964-09-22 Nopco Chem Co Process for the preparation of pantothenic acid salts
WO2001049671A1 (en) * 1999-12-29 2001-07-12 Oxis Isle Of Man, Limited Methods for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1033652B (en) * 1954-09-09 1958-07-10 Upjohn Co Process for the resolution of racemic ª ‡ -oxy-ª ‰, ª ‰ -dimethyl-ª † -butyrolactone into its d (-) - and 1 (+) - stereomers
US2967869A (en) * 1958-06-19 1961-01-10 Nopco Chem Co Process for obtaining d(-)-alpha-hydroxy-beta, beta-dimethyl-gamma-butyrolactone
US3009922A (en) * 1958-06-19 1961-11-21 Nopco Chem Co Process for obtaining d(-)-alpha-hydroxy-beta, beta-dimethyl-gamma-butyrolactone
US3150175A (en) * 1961-08-28 1964-09-22 Nopco Chem Co Process for the preparation of pantothenic acid salts
WO2001049671A1 (en) * 1999-12-29 2001-07-12 Oxis Isle Of Man, Limited Methods for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones
US6613919B2 (en) 1999-12-29 2003-09-02 Oxis Isle Of Man Method for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones

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