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1. (WO2007009953) PROCESS FOR PREPARING 2-METHOXYCARBONYLMETHYL-6,6-DIMETHYL-2- TETRAHYDROPYRAN CARBOXYLIC ACID
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/2007/009953 International Application No.: PCT/EP2006/064273
Publication Date: 25.01.2007 International Filing Date: 14.07.2006
IPC:
C07D 309/08 (2006.01) ,C07C 211/35 (2006.01) ,C07D 491/20 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
309
Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
02
having no double bonds between ring members or between ring members and non-ring members
08
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
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
211
Compounds containing amino groups bound to a carbon skeleton
33
having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
34
of a saturated carbon skeleton
35
containing only non-condensed rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
491
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/-C07D459/290
12
in which the condensed system contains three hetero rings
20
Spiro-condensed systems
Applicants:
ERREGIERRE S.p.A. [IT/IT]; Via Francesco Baracca 19 I-24060 San Paolo D'argon, IT (AllExceptUS)
STRAGEN PHARMA SA [CH/CH]; Rue Hugo De Senger, 3 CH-1205 Geneve, CH (AllExceptUS)
FERRARI, Massimo [IT/IT]; IT (UsOnly)
BELOTTI, Paolo [IT/IT]; IT (UsOnly)
Inventors:
FERRARI, Massimo; IT
BELOTTI, Paolo; IT
Agent:
GERVASI, Gemma ; Corso Di Porta Vittoria 9 I-20122 Milan, IT
Priority Data:
MI2005A00135215.07.2005IT
Title (EN) PROCESS FOR PREPARING 2-METHOXYCARBONYLMETHYL-6,6-DIMETHYL-2- TETRAHYDROPYRAN CARBOXYLIC ACID
(FR) PROCEDE DE PREPARATION D'ACIDE 2-METHOXYCARBONYLMETHYL-6,6-DIMETHYL-2- TETRAHYDROPYRAN CARBOXYLIQUE
Abstract:
(EN) Process for preparing 2-methoxycarbonylmethyl-6,6-dimethyl-2-tetrahydropyran carboxylic acid (I) comprising: a) Reaction of 5-bromo-2-methyl-2-pentene (III) with magnesium and then diethyloxalate to obtain ethyl-2-oxo-6-methyl-5-heptenoate (IV); b) Reaction of ethyl-2-oxo-6-methyl-5-heptenoate (IV) with an alkali amide and methyl acetate to obtain ethyl-2- methoxycarbonylmethyl^-hydroxy-&thetas;-methyl- 5-heptenoate (V); c) Reaction of ethyl-2- methoxycarbonylmethyl-2-hydroxy-6-methyl-5-heptenoate (V) with an alkali metal hydroxide to obtain the corresponding 2-carboxymethyl- 2-hydroxy-6-methyl-5-heptenoic acid (Vl); d) Cyclisation of 2-carboxymethyl-2-hydroxy-6-methyl-5-heptenoic acid (Vl) with formic acid to give 2-carboxymethyl-6,6-dimethyl-2-tetrahydropyrancarboxylic acid (VII); e) Monoesterification of 2-carboxymethyl-6,6-dimethyl-2- tetrahydropyrancarboxylic acid (VII) to 2-methoxycarbonylmethyl-6,6-dimethyl- 2-tetrahydropyran carboxylic acid (I), characterised in that in stage (e) the 2-methoxycarbonylmethyI-6,6-dimethyl-2- tetrahydropyran carboxylic acid (I) is purified by means of the formation of the corresponding salt with cyclohexylamine (IA).
(FR) L'invention concerne un procédé de préparation d'acide 2-methoxycarbonylmethyl-6,6-dimethyl-2-tetrahydropyran carboxylique (I). Ce procédé consiste à (a) mettre en réaction 5-bromo-2-methyl-2-pentène (III) avec du magnésium puis avec du diéthyloxalate pour obtenir ethyl-2-oxo-6-methyl-5-hepténoate (IV); b) à mettre en réaction ethyl-2-oxo-6-methyl-5-hepténoate (IV) avec un amide alcalin et un acétate de méthyle pour obtenir ethyl-2- methoxycarbonylmethyl-hydroxy-?-methyl- 5-hepténoate (V); c) à mettre en réaction ethyl-2- methoxycarbonylmethyl-2-hydroxy-6-methyl-5-heptenoate (V) avec un hydroxyde métallique alcalin pour obtenir l'acide 2-carboxymethyl- 2-hydroxy-6-methyl-5-heptenoïque correspondant (Vl); d) à procéder au cyclage de l'acide 2-carboxymethyl-2-hydroxy-6-methyl-5-heptenoïque (Vl) avec l'acide formique pour obtenir l'acide 2-carboxymethyl-6,6-dimethyl-2-tetrahydropyrancarboxylique (VII); e) à assurer la monoestérification de l'acide 2-carboxymethyl-6,6-dimethyl-2- tetrahydropyrancarboxylique (VII) en acide 2-methoxycarbonylmethyl-6,6-dimethyl- 2-tetrahydropyran carboxylique (I), le procédé étant caractérisé en ce que, à l'étape (E), l'acide 2-methoxycarbonylmethyI-6,6-dimethyl-2- tetrahydropyran carboxylique (I) est purifié par la formation du sel correspondant avec la cyclohexylamine (IA).
Designated States: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
EP1907371JP2009501196US20090043093ES2378081CN101233123PT1907371
DK1907371