GB1287839A - - Google Patents

Info

Publication number
GB1287839A
GB1287839A GB5640770A GB5640770A GB1287839A GB 1287839 A GB1287839 A GB 1287839A GB 5640770 A GB5640770 A GB 5640770A GB 5640770 A GB5640770 A GB 5640770A GB 1287839 A GB1287839 A GB 1287839A
Authority
GB
United Kingdom
Prior art keywords
formula
salts
cis
antipode
trione
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
GB5640770A
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 filed Critical
Publication of GB1287839A publication Critical patent/GB1287839A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, 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
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

1287839 (+) - Cis - 1,3 - dibenzyl - hexahydro - 1 H - furo[3,4 - d]imidazole - 2,4 - dione F. HOFFMAN-LA ROCHE & CO AG 27 Nov 1970 [29 Nov 1969] 56407/70 Headings C2C and C2U (+) - Cis - 1,3 - dibenzyl - hexahydro - 1H- furo[3,4-d]imidazole-2,4-dione of the formula wherein the rings A and B are cis-linked and R represents benzyl, may be obtained by converting the trione of formula by means of cholesterol or cyclohexanol into the corresponding half-esters of the formulµ wherein R 1 represents the cholesteryl or cyclohexyl residue, separating the cholesterol halfesters from each other by fractional crystallization of their triethylamine salts and the cyclohexyl half-esters from each other by fractional crystallization of their ephedrine salts, converting the salts of the desired antipode thus obtained into the compound of Formula I, and optionally hydrolysing the salts of the undesired antipode and recycling the racemate, after conversion into the trione of Formula (II), into the process. The salts of the desired antipode of Formula (III) or (IV) may be converted into the product of Formula (I) by treatment with LiBH 4 which may be formed in situ.
GB5640770A 1969-11-29 1970-11-27 Expired GB1287839A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1777269A CH565798A5 (en) 1969-11-29 1969-11-29

Publications (1)

Publication Number Publication Date
GB1287839A true GB1287839A (en) 1972-09-06

Family

ID=4427992

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5640770A Expired GB1287839A (en) 1969-11-29 1970-11-27

Country Status (10)

Country Link
JP (1) JPS4932551B1 (en)
BE (1) BE759512A (en)
CA (1) CA983938A (en)
CH (1) CH565798A5 (en)
DE (1) DE2058248C3 (en)
DK (1) DK143109C (en)
FR (1) FR2077539B1 (en)
GB (1) GB1287839A (en)
NL (1) NL159385B (en)
SE (1) SE391718B (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0081047B1 (en) * 1981-12-07 1985-12-18 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Process for the preparation of an optically active lactone, and starting products for the process
DE3150723A1 (en) * 1981-12-22 1983-06-30 Basf Ag, 6700 Ludwigshafen IMPROVED METHOD FOR PRODUCING 1,3-DISUBSTITUTED 4,5-CIS-DICARBOXY-2-IMIDAZOLIDONES
CH670644A5 (en) * 1986-12-18 1989-06-30 Lonza Ag
CH671227A5 (en) * 1986-12-02 1989-08-15 Lonza Ag
US5162540A (en) * 1986-12-18 1992-11-10 Lonza Ltd. Process for the production of (+) biotin
FI95034C (en) * 1989-03-15 1995-12-11 Lonza Ag Process for the preparation of 1,3-substituted tetrahydro-1H-thieno / 3,4-d / imidazole-2 (3H) -one-4-ylidene pentanoic acid ester
FI935609A (en) * 1992-12-18 1994-06-19 Lonza Ag Asymmetric hydrogenation of dihydrofuroimidazole derivatives
CA2134441A1 (en) * 1993-04-20 1994-10-27 Martin Eyer Asymmetric hydrogenation of furoimidazole derivatives
CA2122511A1 (en) * 1993-05-14 1994-11-15 John Mcgarrity Asymmetric hydrogenation of furoimidazole derivatives
DE10033284A1 (en) * 2000-07-07 2002-01-17 Merck Patent Gmbh Process for the production of (+) - biotin
TW200300676A (en) 2001-12-04 2003-06-16 Tanabe Seiyaku Co Biotin intermediate and its production
CN113121549B (en) * 2019-12-31 2022-08-26 江西天新药业股份有限公司 Method for stereoselectively synthesizing chiral lactone, chiral compound and application thereof

Also Published As

Publication number Publication date
CH565798A5 (en) 1975-08-29
CA983938A (en) 1976-02-17
NL7015355A (en) 1971-06-02
DE2058248C3 (en) 1980-12-18
JPS4932551B1 (en) 1974-08-31
FR2077539A1 (en) 1971-10-29
DK143109C (en) 1981-09-21
DK143109B (en) 1981-03-30
FR2077539B1 (en) 1973-02-02
BE759512A (en) 1971-05-27
NL159385B (en) 1979-02-15
DE2058248B2 (en) 1980-04-10
DE2058248A1 (en) 1971-06-09
SE391718B (en) 1977-02-28

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Legal Events

Date Code Title Description
PS Patent sealed
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PE20 Patent expired after termination of 20 years