JP2017508783A - 1−インダノールおよび1−インダンアミンを製造する方法 - Google Patents
1−インダノールおよび1−インダンアミンを製造する方法 Download PDFInfo
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- JP2017508783A JP2017508783A JP2016565561A JP2016565561A JP2017508783A JP 2017508783 A JP2017508783 A JP 2017508783A JP 2016565561 A JP2016565561 A JP 2016565561A JP 2016565561 A JP2016565561 A JP 2016565561A JP 2017508783 A JP2017508783 A JP 2017508783A
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- Prior art keywords
- hydrogen
- alkyl
- process according
- methyl
- mol
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- 238000000034 method Methods 0.000 title claims abstract description 17
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 title claims abstract description 11
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 43
- 229910052763 palladium Inorganic materials 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 16
- -1 2,2-dimethylpropanoyl Chemical group 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 229950010765 pivalate Drugs 0.000 claims description 2
- 101150003085 Pdcl gene Proteins 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 19
- 238000006254 arylation reaction Methods 0.000 abstract description 5
- 239000013543 active substance Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- XJUZBQOHVBXJSY-UHFFFAOYSA-N C(C(C)(C)C)(=O)OC1C=CC2=CC=CC=C12 Chemical compound C(C(C)(C)C)(=O)OC1C=CC2=CC=CC=C12 XJUZBQOHVBXJSY-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 2
- 125000005547 pivalate group Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- MGHNDJJPPOAIHK-UHFFFAOYSA-N 1H-inden-1-yl Chemical group C1=CC=C2[CH]C=CC2=C1 MGHNDJJPPOAIHK-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- OYDHJXAKZYCIRL-UHFFFAOYSA-N 2-(2,6-dimethyl-2,3-dihydro-1H-inden-1-yl)isoindole-1,3-dione Chemical compound CC1C(C2=CC(=CC=C2C1)C)N1C(C2=CC=CC=C2C1=O)=O OYDHJXAKZYCIRL-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- UTJKNXNXHSAHQG-UHFFFAOYSA-N 2-[1-(2-bromophenyl)-2,2-dimethylpropyl]isoindole-1,3-dione Chemical compound CC(C)(C)C(N1C(=O)C2=CC=CC=C2C1=O)C1=C(Br)C=CC=C1 UTJKNXNXHSAHQG-UHFFFAOYSA-N 0.000 description 1
- QSHLLIDPJRCCEA-UHFFFAOYSA-N 2-[1-(2-bromophenyl)-2-methylpropyl]isoindole-1,3-dione Chemical compound CC(C)C(N1C(=O)C2=CC=CC=C2C1=O)C1=C(Br)C=CC=C1 QSHLLIDPJRCCEA-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- GNETVOUSGGAEDK-UHFFFAOYSA-N 4-bis[4-(dimethylamino)phenyl]phosphanyl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1P(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 GNETVOUSGGAEDK-UHFFFAOYSA-N 0.000 description 1
- LTGCBSAMUKTKST-UHFFFAOYSA-N 5-(2-bromophenyl)-4,4-dimethyloxolan-2-one Chemical compound CC1(C)CC(=O)OC1C1=C(Br)C=CC=C1 LTGCBSAMUKTKST-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FAIZMNAGGDXJCD-UHFFFAOYSA-N CC(C)(C)C(O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C1=C(Br)C=CC(F)=C1 Chemical compound CC(C)(C)C(O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C1=C(Br)C=CC(F)=C1 FAIZMNAGGDXJCD-UHFFFAOYSA-N 0.000 description 1
- XLWWAPXXGJJGIW-UHFFFAOYSA-N CC(C)C(O[Si](C(C)C)(C(C)C)C(C)C)C1=C(Br)C=CC=C1 Chemical compound CC(C)C(O[Si](C(C)C)(C(C)C)C(C)C)C1=C(Br)C=CC=C1 XLWWAPXXGJJGIW-UHFFFAOYSA-N 0.000 description 1
- XXYPNTAYZPHERE-UHFFFAOYSA-N CC(C)[Si](OCCC1(CC1)C1=C(Br)C=CC=C1)(C(C)C)C(C)C Chemical compound CC(C)[Si](OCCC1(CC1)C1=C(Br)C=CC=C1)(C(C)C)C(C)C XXYPNTAYZPHERE-UHFFFAOYSA-N 0.000 description 1
- APYOUWABGRDMOF-UHFFFAOYSA-N CC(C1)(C[BrH]c2cccnc22)C2OC1=O Chemical compound CC(C1)(C[BrH]c2cccnc22)C2OC1=O APYOUWABGRDMOF-UHFFFAOYSA-N 0.000 description 1
- UMTYELLZEFBCRN-UHFFFAOYSA-N COC1=CC(C(O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)=C(Br)C=C1 Chemical compound COC1=CC(C(O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)=C(Br)C=C1 UMTYELLZEFBCRN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 0 O=C(CCCI*1C2)O[C@@]1c1c2ccc(F)c1 Chemical compound O=C(CCCI*1C2)O[C@@]1c1c2ccc(F)c1 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910021605 Palladium(II) bromide Inorganic materials 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UEEXVJGALQUXKO-UHFFFAOYSA-N [1-(2-bromo-4,5-dimethoxyphenyl)-2,2-dimethylpropoxy]-tritert-butylsilane Chemical compound BrC1=C(C=C(C(=C1)OC)OC)C(C(C)(C)C)O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C UEEXVJGALQUXKO-UHFFFAOYSA-N 0.000 description 1
- MOCUOYKGMQLDNM-UHFFFAOYSA-N [1-(2-bromo-5-fluorophenyl)-2,2-dimethylpropyl] 2,2-dimethylpropanoate Chemical compound CC(C(=O)OC(C(C)(C)C)C1=C(C=CC(=C1)F)Br)(C)C MOCUOYKGMQLDNM-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- WXMZPPIDLJRXNK-UHFFFAOYSA-N butyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCC)C1=CC=CC=C1 WXMZPPIDLJRXNK-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- WFMNHCSATCWAAQ-UHFFFAOYSA-M potassium;2,2-dimethylpropanoate Chemical compound [K+].CC(C)(C)C([O-])=O WFMNHCSATCWAAQ-UHFFFAOYSA-M 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- SJRDNQOIQZOVQD-UHFFFAOYSA-M sodium;2,2-dimethylpropanoate Chemical compound [Na+].CC(C)(C)C([O-])=O SJRDNQOIQZOVQD-UHFFFAOYSA-M 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- FCZNGMZRLGOAQE-UHFFFAOYSA-N spiro[1,2-dihydroindene-3,1'-cyclopropane] Chemical compound C1CC11C2=CC=CC=C2CC1 FCZNGMZRLGOAQE-UHFFFAOYSA-N 0.000 description 1
- YDJXDYKQMRNUSA-UHFFFAOYSA-N tri(propan-2-yl)silane Chemical compound CC(C)[SiH](C(C)C)C(C)C YDJXDYKQMRNUSA-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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Abstract
Description
Yは、NR1R2またはOR3であり、
R1は、水素もしくはCOR4であり、
R2は、COR4であり、
またはR1およびR2は、COCH2CH2CO基もしくはCO−フェニレン−CO基を共に形成し、
R3は、Si(R5)3またはピバロイル(2,2−ジメチルプロパノイル)であり、
R4は、(C1−C6)−アルキルまたはフェニルであり、
R5は、(C1−C6)−アルキルまたはフェニルであり、
Halは、塩素、臭素またはヨウ素であり、
Rは、フッ素、(C1−C3)−アルキルまたは(C1−C3)−アルコキシであり、
X1は、水素もしくは(C1−C6)−アルキルであり、
X2は、水素もしくは(C1−C6)−アルキルであり、
X3は、水素もしくは(C1−C6)−アルキルであり、
X4は、水素もしくは(C1−C6)−アルキルであり、
または
X1およびX2、もしくは
X3およびX4、もしくは
X1およびX3は、それらが結合している炭素原子と共に、各々の場合に3員から7員の飽和環を形成し、
または
YおよびX1は、それらが結合している炭素原子と共に、5員から7員の飽和環を形成し、
mは、0、1、2または3である。
Yは、NR1R2またはOR3であり、
R1は、水素またはCOR4であり、
R2は、COR4であり、
R3は、Si(R5)3または2,2−ジメチルプロパノイルであり、
R4は、tert−ブチルであり、
R5は、イソプロピルであり、
Halは、臭素またはヨウ素であり、
Rは、フッ素、メチルまたはメトキシであり、
X1は、水素もしくはメチルであり、
X2は、水素もしくはメチルであり、
X3は、水素もしくはメチルであり、
X4は、水素もしくはメチルであり、
または
X1およびX2、もしくは
X3およびX4、もしくは
X1およびX3は、それらが結合している炭素原子と共に、各々の場合に3員から7員の飽和環を形成し、
または
YおよびX1は、それらが結合している炭素原子と共に、5員から7員の飽和環を形成し、
mは、0、1、2または3である。
Ac アセテート Cy シクロヘキシル Cyp シクロペンチル
Me メチル Ph フェニル Piv ピバレート
TiPs トリイソプロピルシリル
である。
不活性ガス下、パラジウム触媒(0.015mmol、5mol%)、任意選択でホスフィンリガンド(0.03mmol、10mol%)、および塩基、例としてピバリン酸カリウム(0.030mmol、10mol%)およびK2CO3(0.3mmol、1.0当量)を導入し、溶媒(3mlのキシレン)および式(II)の化合物(0.3mmol、1.0当量)を加える。混合物を次いで室温で10分間撹拌し、続いて140℃まで加熱し、この温度で16時間撹拌する。反応混合物を室温まで冷却した後にろ過し、溶媒を取り去り、残渣をクロマトグラフィーにより精製する。
実施例2:[1−(2−ブロモフェニル)−シクロプロピルエトキシ](トリイソプロピル)シランからの((2’,3’−ジヒドロスピロ[シクロプロパン−1,1’−インデン]−3’−イル)オキシ)トリイソプロピルシランの調製
実施例3:[1−(2−ブロモ−4,5−ジメトキシフェニル)−2,2−ジメチルプロポキシ](トリ−tert−ブチル)シランからの((5,6−ジメトキシ−2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル)オキシ)トリイソプロピルシランの調製
実施例4:[1−(2−ブロモ−5−メトキシフェニル)−2,2−ジメチルプロポキシ](トリ−tert−ブチル)シランからの((6−メトキシ−2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル)オキシ)トリイソプロピルシランの調製
実施例5:[1−(2−ブロモ−5−フルオロフェニル)−2,2−ジメチルプロポキシ](トリ−tert−ブチル)シランからの((6−フルオロ−2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル)オキシ)トリイソプロピルシランの調製
実施例6:1−(2−ブロモフェニル)−2,2−ジメチルプロピル 2,2−ジメチルプロパノエートからの2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル 2,2−ジメチルプロパノエートの調製
実施例7:1−(2−ブロモ−5−メトキシフェニル)−2,2−ジメチルプロピル 2,2−ジメチルプロパノエートからの6−メトキシ−2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル 2,2−ジメチルプロパノエートの調製
実施例8:1−(2−ブロモ−5−フルオロフェニル)−2,2−ジメチルプロピル 2,2−ジメチルプロパノエートからの6−フルオロ−2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル 2,2−ジメチルプロパノエートの調製
実施例9:5−(2−ブロモフェニル)−4,4−ジメチルジヒドロフラン−2(3H)−オンからの(3aR*,8bS*)−3a−メチル−3,3a,4,8b−テトラヒドロ−2H−インデノ[1,2−b]フラン−2−オンの調製
実施例10:2−[1−(2−ブロモフェニル)−2−メチルプロピル]−1H−イソインドール−1,3(2H)−ジオンからの2−(2−メチル−2,3−ジヒドロ−1H−インデン−1−イル)イソインドリン−1,3−ジオンの調製
実施例11:2−[1−(2−ブロモフェニル)−2,2−ジメチルプロピル]−1H−イソインドール−1,3(2H)−ジオンからの2−(2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル)イソインドリン−1,3−ジオンの調製
実施例12:2−[1−(2−ブロモ−5−メチルフェニル)−2−メチルプロピル]−1H−イソインドール−1,3(2H)−ジオンからの2−[(1R,2S)−2,6−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル]−1H−イソインドール−1,3(2H)−ジオンを介した(1R,2S)−2,6−ジメチルインダン−1−アミンの調製
次いで、1mlのメタノールおよび1mlのTHF中0.17mmolの2−(2,6−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル)イソインドリン−1,3−ジオンの溶液を、0℃で、1.7mmolのヒドラジン水和物と混ぜた。混合物を次いで室温で12時間撹拌した。混合物をろ過し、濃縮した。残渣をDCMと水との間で分画し、有機相を分離し、飽和NaHCO3で洗浄した。MgSO4での乾燥および濃縮後、生成物を固形物として98%の収率で得た。
実施例13:[1−(2−ブロモフェニル)−2−メチルプロポキシ](トリイソプロピル)シランからのトリイソプロピル((2−メチル−2,3−ジヒドロ−1H−インデン−1−イル)オキシ)シランの調製
トランス異性体:1H NMR(300MHz,CDCl3,293K) δ1.05−1.31(m,24H),2.34−2.57(m,2H),3.10−3.33(m,1H),4.98(d,J=5.0Hz,1H),7.19−7.28(m,3H),7.37−7.46(m,1H).
Claims (11)
- 一般式(I)の1−インダノールおよび1−インダンアミンを調製する方法であって、
1−(2−ハロフェニル)アルカン−1−オールまたは1−(2−ハロフェニル)アルカン−1−アミン(II)を高温で、パラジウム触媒作用の下、ホスフィンリガンド、塩基および溶媒の存在下で反応させることを含む方法。
Yは、NR1R2またはOR3であり、
R1は、水素もしくはCOR4であり、
R2は、COR4であり、
またはR1およびR2は、COCH2CH2CO基もしくはCO−フェニレン−CO基を共に形成し、
R3は、Si(R5)3または2,2−ジメチルプロパノイルであり、
R4は、(C1−C6)−アルキルまたはフェニルであり、
R5は、(C1−C6)−アルキルまたはフェニルであり、
Halは、塩素、臭素またはヨウ素であり、
Rは、フッ素、(C1−C3)−アルキルまたは(C1−C3)−アルコキシであり、
X1は、水素もしくは(C1−C6)−アルキルであり、
X2は、水素もしくは(C1−C6)−アルキルであり、
X3は、水素もしくは(C1−C6)−アルキルであり、
X4は、水素もしくは(C1−C6)−アルキルであり、
または
X1およびX2、もしくは
X3およびX4、もしくは
X1およびX3は、それらが結合している炭素原子と共に、各々の場合に3員から7員の飽和環を形成し、
または
YおよびX1は、それらが結合している炭素原子と共に、5員から7員の飽和環を形成し、
mは、0、1、2または3である。] - 式中、ラジカル、記号および指数が以下の定義を有する、請求項1に記載の方法:
Yが、NR1R2またはOR3であり、
R1は、水素またはCOR4であり、
R2は、COR4であり、
R3は、Si(R5)3または2,2−ジメチルプロパノイルであり、
R4は、tert−ブチルであり、
R5は、イシソプロピル(isisopropyl)であり、
Halが、臭素またはヨウ素であり、
Rが、フッ素、メチルまたはメトキシであり、
X1が、水素もしくはメチルであり、
X2が、水素もしくはメチルであり、
X3が、水素もしくはメチルであり、
X4が、水素もしくはメチルであり、
または
X1およびX2、もしくは
X3およびX4、もしくは
X1およびX3が、それらが結合している炭素原子と共に、各々の場合に3員から7員の飽和環を形成し、
または
YおよびX1が、それらが結合している炭素原子と共に、5員から7員の飽和環を形成し、
mが、0、1、2または3である。 - 用いられる前記パラジウム触媒が、Pd(OAc)2、トリス(ジベンジリデンアセトン)ジパラジウム(0)、PdCl2およびPdBr2よりなる群からの化合物である、請求項1または2に記載の方法。
- Pd(OAc)2が用いられる、請求項3に記載の方法。
- トリフェニルホスフィンがリガンドとして用いられる、請求項1から4のいずれかに記載の方法。
- テトラキス(トリフェニルホスフィニル)パラジウムが、組み合わされたパラジウム触媒およびリガンドとして用いられる、請求項1から5のいずれかに記載の方法。
- 前記パラジウム触媒およびリガンド、または、それらの前記組み合わせが、各々の場合において、化合物(II)に基づき、0.1から10mol%の量で用いられる、請求項1から6のいずれかに記載の方法。
- 前記パラジウム触媒およびリガンド、または、それらの前記組み合わせが、各々の場合において、化合物(II)に基づき、1から5mol%の量で用いられる、請求項7に記載の方法。
- 用いられる前記塩基が、アルカリ金属の炭酸塩およびアルカリ金属のピバリン酸塩の混合物である、請求項1から8のいずれかに記載の方法。
- 前記塩基が、化合物(II)に基づき、1から5モルの割合で用いられる、請求項1から8のいずれかに記載の方法。
- 用いられる前記溶媒が芳香族化合物の群からのものである、請求項1から10のいずれかに記載の方法。
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EP3099671A1 (de) | 2016-12-07 |
WO2015113903A1 (de) | 2015-08-06 |
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US20160340370A1 (en) | 2016-11-24 |
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TWI668201B (zh) | 2019-08-11 |
EP3099671B1 (de) | 2017-12-27 |
CN106414420A (zh) | 2017-02-15 |
BR112016017513B1 (pt) | 2022-03-03 |
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US9796737B2 (en) | 2017-10-24 |
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CN106414420B (zh) | 2018-12-14 |
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