NO860007L

NO860007L - Fremgangsmaate til fremstilling av nye trisubstituerte azacykloalkaner, resp. azacykloalkener.

Fremgangsmaate til fremstilling av nye trisubstituerte azacykloalkaner, resp. azacykloalkener.

Info

Publication number: NO860007L
Authority: NO; Norway
Prior art keywords: ethyl; indol; carboxylic acid; hydroxy; ester
Prior art date: 1985-01-03

Application number

NO860007A

Other languages

English (en)

Norwegian (no)

Inventor

Wolfgang Froestl

Beat Schmitz

Angelo Storni

Original Assignee

Ciba Geigy Ag

Priority date

1985-01-03

Filing date

1986-01-02

Publication date

1986-07-04

1986-01-02 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1986-07-04 Publication of NO860007L publication Critical patent/NO860007L/no

Links

238000000034 method Methods 0.000 title claims description 88
238000002360 preparation method Methods 0.000 title claims description 40
150000003976 azacycloalkanes Chemical class 0.000 title claims description 3
-1 3-indolyl residue Chemical group 0.000 claims description 269
150000001875 compounds Chemical class 0.000 claims description 243
150000003839 salts Chemical class 0.000 claims description 133
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 101
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 87
125000004432 carbon atom Chemical group C* 0.000 claims description 78
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 76
239000002253 acid Substances 0.000 claims description 74
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 69
125000000217 alkyl group Chemical group 0.000 claims description 61
229910052739 hydrogen Inorganic materials 0.000 claims description 58
239000000203 mixture Substances 0.000 claims description 58
239000001257 hydrogen Substances 0.000 claims description 56
229910052736 halogen Inorganic materials 0.000 claims description 52
150000002367 halogens Chemical class 0.000 claims description 47
229910052757 nitrogen Inorganic materials 0.000 claims description 44
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 37
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 34
239000005977 Ethylene Substances 0.000 claims description 32
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 30
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 24
125000002947 alkylene group Chemical group 0.000 claims description 23
229910052740 iodine Inorganic materials 0.000 claims description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
150000002148 esters Chemical class 0.000 claims description 18
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 16
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 13
150000001335 aliphatic alkanes Chemical class 0.000 claims description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 10
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
125000004423 acyloxy group Chemical group 0.000 claims description 9
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 8
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
241000534944 Thia Species 0.000 claims description 7
150000001450 anions Chemical class 0.000 claims description 7
XIWBSOUNZWSFKU-UHFFFAOYSA-N ethyl piperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCNC1 XIWBSOUNZWSFKU-UHFFFAOYSA-N 0.000 claims description 7
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 5
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 5
150000003840 hydrochlorides Chemical class 0.000 claims description 5
BCDBHIAXYFPJCT-UHFFFAOYSA-N methyl piperidine-3-carboxylate Chemical compound COC(=O)C1CCCNC1 BCDBHIAXYFPJCT-UHFFFAOYSA-N 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
229940109275 cyclamate Drugs 0.000 claims description 3
DYPLDWLIOGXSSE-UHFFFAOYSA-N guvacoline Chemical compound COC(=O)C1=CCCNC1 DYPLDWLIOGXSSE-UHFFFAOYSA-N 0.000 claims description 3
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
DBJSKLKTQJMDTJ-UHFFFAOYSA-N ethyl 1,2,3,6-tetrahydropyridine-5-carboxylate Chemical compound CCOC(=O)C1=CCCNC1 DBJSKLKTQJMDTJ-UHFFFAOYSA-N 0.000 claims description 2
LGLCCOXWWZVQGP-UHFFFAOYSA-N ethyl 4-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-2,5-dihydropyrrole-3-carboxylate Chemical compound C(C)OC(=O)C=1CN(CC=1O)CCC1=CNC2=CC=CC=C12 LGLCCOXWWZVQGP-UHFFFAOYSA-N 0.000 claims description 2
GNZMQMYTGQDFSY-GDBMZVCRSA-N methyl (3R,4R)-1-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-hydroxypiperidine-3-carboxylate Chemical compound COC(=O)[C@@H]1CN(CC[C@H]1O)CCC1=CNC2=CC=C(C=C12)Cl GNZMQMYTGQDFSY-GDBMZVCRSA-N 0.000 claims description 2
241000231697 Zelus means Species 0.000 claims 1
125000001118 alkylidene group Chemical group 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
XGTHADOPJXOSOC-NVXWUHKLSA-N ethyl (3R,4R)-1-[2-(5-chloro-1H-indol-3-yl)ethyl]-4-hydroxypiperidine-3-carboxylate Chemical compound C(C)OC(=O)[C@@H]1CN(CC[C@H]1O)CCC1=CNC2=CC=C(C=C12)Cl XGTHADOPJXOSOC-NVXWUHKLSA-N 0.000 claims 1
OJYJSEKEBGLSKC-UHFFFAOYSA-N methyl 4-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-2,5-dihydropyrrole-3-carboxylate Chemical compound COC(=O)C=1CN(CC=1O)CCC1=CNC2=CC=CC=C12 OJYJSEKEBGLSKC-UHFFFAOYSA-N 0.000 claims 1
XBNGBGYWMXBQRX-UHFFFAOYSA-N methyl 4-oxopiperidine-3-carboxylate Chemical compound COC(=O)C1CNCCC1=O XBNGBGYWMXBQRX-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 113
239000000243 solution Substances 0.000 description 85
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
238000006243 chemical reaction Methods 0.000 description 70
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 52
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
238000003756 stirring Methods 0.000 description 43
239000002585 base Substances 0.000 description 37
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
239000012074 organic phase Substances 0.000 description 33
238000001816 cooling Methods 0.000 description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
229910052783 alkali metal Inorganic materials 0.000 description 29
239000002904 solvent Substances 0.000 description 29
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
150000007513 acids Chemical class 0.000 description 28
239000003795 chemical substances by application Substances 0.000 description 28
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
239000003921 oil Substances 0.000 description 24
239000007858 starting material Substances 0.000 description 24
150000001340 alkali metals Chemical class 0.000 description 22
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
229910052938 sodium sulfate Inorganic materials 0.000 description 20
235000011152 sodium sulphate Nutrition 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
238000010438 heat treatment Methods 0.000 description 17
230000007062 hydrolysis Effects 0.000 description 17
238000006460 hydrolysis reaction Methods 0.000 description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
229910052801 chlorine Inorganic materials 0.000 description 15
229910052500 inorganic mineral Inorganic materials 0.000 description 15
235000010755 mineral Nutrition 0.000 description 15
239000011707 mineral Substances 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
125000002252 acyl group Chemical group 0.000 description 14
150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
238000000354 decomposition reaction Methods 0.000 description 14
239000003480 eluent Substances 0.000 description 14
239000012279 sodium borohydride Substances 0.000 description 14
229910000033 sodium borohydride Inorganic materials 0.000 description 14
229910021529 ammonia Inorganic materials 0.000 description 13
235000019439 ethyl acetate Nutrition 0.000 description 13
125000004043 oxo group Chemical group O=* 0.000 description 13
235000011181 potassium carbonates Nutrition 0.000 description 13
239000000725 suspension Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
239000013543 active substance Substances 0.000 description 12
239000011261 inert gas Substances 0.000 description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
235000011121 sodium hydroxide Nutrition 0.000 description 12
QMDFHZOGAYONLN-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-3-carboxylic acid Chemical compound OC(=O)C1CNC=CC1 QMDFHZOGAYONLN-UHFFFAOYSA-N 0.000 description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
150000001408 amides Chemical class 0.000 description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 11
229910052794 bromium Inorganic materials 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
229940086542 triethylamine Drugs 0.000 description 11
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
150000008044 alkali metal hydroxides Chemical class 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
239000000825 pharmaceutical preparation Substances 0.000 description 10
238000012546 transfer Methods 0.000 description 10
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
230000002378 acidificating effect Effects 0.000 description 9
125000001931 aliphatic group Chemical group 0.000 description 9
150000003973 alkyl amines Chemical class 0.000 description 9
150000001735 carboxylic acids Chemical class 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
229910052784 alkaline earth metal Inorganic materials 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
239000005909 Kieselgur Substances 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
125000004494 ethyl ester group Chemical group 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
150000004820 halides Chemical class 0.000 description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
125000001841 imino group Chemical group [H]N=* 0.000 description 7
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
150000001342 alkaline earth metals Chemical class 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000003776 cleavage reaction Methods 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
239000000155 melt Substances 0.000 description 6
150000004702 methyl esters Chemical class 0.000 description 6
235000006408 oxalic acid Nutrition 0.000 description 6
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 6
229910003446 platinum oxide Inorganic materials 0.000 description 6
238000000746 purification Methods 0.000 description 6
230000007017 scission Effects 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000002841 Lewis acid Substances 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
150000004649 carbonic acid derivatives Chemical class 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
239000001530 fumaric acid Substances 0.000 description 5
150000002430 hydrocarbons Chemical group 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
150000007517 lewis acids Chemical class 0.000 description 5
125000001477 organic nitrogen group Chemical group 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
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