CN103073495B - 一种ent-3-甲氧基吗喃的制备方法 - Google Patents
一种ent-3-甲氧基吗喃的制备方法 Download PDFInfo
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- CN103073495B CN103073495B CN201310046837.5A CN201310046837A CN103073495B CN 103073495 B CN103073495 B CN 103073495B CN 201310046837 A CN201310046837 A CN 201310046837A CN 103073495 B CN103073495 B CN 103073495B
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- benzyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 8
- 238000005574 benzylation reaction Methods 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- 238000006264 debenzylation reaction Methods 0.000 claims abstract description 7
- 238000007069 methylation reaction Methods 0.000 claims abstract description 7
- NDEKWGRSBBCVEX-UHFFFAOYSA-N 1,2-dibenzyl-3,4,5,6,7,8-hexahydro-1H-isoquinoline Chemical compound C(C1=CC=CC=C1)C1N(CCC=2CCCCC1=2)CC1=CC=CC=C1 NDEKWGRSBBCVEX-UHFFFAOYSA-N 0.000 claims abstract description 6
- MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 claims abstract description 5
- 229960001985 dextromethorphan Drugs 0.000 claims abstract description 5
- QYXMTRMBTVDSOQ-UHFFFAOYSA-N 1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline Chemical compound N1CCC(CCCC2)=C2C1CC1=CC=CC=C1 QYXMTRMBTVDSOQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000006722 reduction reaction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- 229940073608 benzyl chloride Drugs 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003610 charcoal Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract 3
- MKXZASYAUGDDCJ-NJAFHUGGSA-N dextromethorphan Chemical compound C([C@@H]12)CCC[C@]11CCN(C)[C@H]2CC2=CC=C(OC)C=C21 MKXZASYAUGDDCJ-NJAFHUGGSA-N 0.000 description 20
- 239000012535 impurity Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- YBYCJQQRZPXLHU-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octahydroisoquinoline Chemical compound C1CNCC2=C1CCCC2 YBYCJQQRZPXLHU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000954 anitussive effect Effects 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000006170 formylation reaction Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012925 reference material Substances 0.000 description 3
- XUKUURHRXDUEBC-SXOMAYOGSA-N (3s,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-SXOMAYOGSA-N 0.000 description 2
- 0 *c1ccc(C[C@]2NCCC3=C2CCCC3)cc1 Chemical compound *c1ccc(C[C@]2NCCC3=C2CCCC3)cc1 0.000 description 2
- AAEQXEDPVFIFDK-UHFFFAOYSA-N 3-(4-fluorobenzoyl)-2-(2-methylpropanoyl)-n,3-diphenyloxirane-2-carboxamide Chemical compound C=1C=CC=CC=1NC(=O)C1(C(=O)C(C)C)OC1(C=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1 AAEQXEDPVFIFDK-UHFFFAOYSA-N 0.000 description 2
- 238000010719 annulation reaction Methods 0.000 description 2
- 229940124584 antitussives Drugs 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000001035 methylating effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- ZYYDNMRUDMCOHG-UHFFFAOYSA-N 1-benzyl-2-methyl-3,4,5,6,7,8-hexahydro-1h-isoquinoline Chemical compound CN1CCC(CCCC2)=C2C1CC1=CC=CC=C1 ZYYDNMRUDMCOHG-UHFFFAOYSA-N 0.000 description 1
- XUDUTRMKKYUAKI-UHFFFAOYSA-N 3-[1-(1-phenylethyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound C1CC(N2C(NC3=CC=CC=C32)=O)CCN1C(C)C1=CC=CC=C1 XUDUTRMKKYUAKI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CRXXSGLBECOUQH-UHFFFAOYSA-N CN1C(Cc(cc2)ccc2OC)C(CCCC2)=C2CC1 Chemical compound CN1C(Cc(cc2)ccc2OC)C(CCCC2)=C2CC1 CRXXSGLBECOUQH-UHFFFAOYSA-N 0.000 description 1
- XSOPBBOEINVWML-UHFFFAOYSA-N COc1ccc(CC(C(CCCC2)=C2CC2)N2C=O)cc1 Chemical compound COc1ccc(CC(C(CCCC2)=C2CC2)N2C=O)cc1 XSOPBBOEINVWML-UHFFFAOYSA-N 0.000 description 1
- FLKXUCHNMMFRRQ-XMMPIXPASA-N COc1ccc(C[C@H]2N(Cc3ccccc3)CCC3=C2CCCC3)cc1 Chemical compound COc1ccc(C[C@H]2N(Cc3ccccc3)CCC3=C2CCCC3)cc1 FLKXUCHNMMFRRQ-XMMPIXPASA-N 0.000 description 1
- NPEVCJZMQGZNET-QGZVFWFLSA-N COc1ccc(C[C@H]2NCCC3=C2CCCC3)cc1 Chemical compound COc1ccc(C[C@H]2NCCC3=C2CCCC3)cc1 NPEVCJZMQGZNET-QGZVFWFLSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229960003406 levorphanol Drugs 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- -1 trimethylphenyl Chemical group 0.000 description 1
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 1
Abstract
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CN103275005B (zh) * | 2013-06-17 | 2015-05-20 | 苏州立新制药有限公司 | ent-3-甲氧基-17-甲基吗喃-10-酮的制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN87107372A (zh) * | 1986-11-07 | 1988-08-03 | 奥里尔股份有限公司 | 制备5.6-二羟基吲哚及其3-烷基衍生物和中间体化合物的方法 |
CN1178218A (zh) * | 1996-10-02 | 1998-04-08 | 霍夫曼-拉罗奇有限公司 | (z)-1-[1-(4-甲氧基亚苄基)-1,2,3,4,5,6,7,8-八氢-异喹啉-2-基]烷酮的生产方法 |
CN1590394A (zh) * | 2003-09-01 | 2005-03-09 | 北京大学 | 新型三糖和五糖寡糖抗原,它们的合成方法以及在制备抑制排斥反应的药物中的用途 |
WO2011032214A1 (en) * | 2009-09-16 | 2011-03-24 | Monash University | A method for the n-demethylation of n-methyl heterocycles |
-
2013
- 2013-02-06 CN CN201310046837.5A patent/CN103073495B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN87107372A (zh) * | 1986-11-07 | 1988-08-03 | 奥里尔股份有限公司 | 制备5.6-二羟基吲哚及其3-烷基衍生物和中间体化合物的方法 |
CN1178218A (zh) * | 1996-10-02 | 1998-04-08 | 霍夫曼-拉罗奇有限公司 | (z)-1-[1-(4-甲氧基亚苄基)-1,2,3,4,5,6,7,8-八氢-异喹啉-2-基]烷酮的生产方法 |
CN1590394A (zh) * | 2003-09-01 | 2005-03-09 | 北京大学 | 新型三糖和五糖寡糖抗原,它们的合成方法以及在制备抑制排斥反应的药物中的用途 |
WO2011032214A1 (en) * | 2009-09-16 | 2011-03-24 | Monash University | A method for the n-demethylation of n-methyl heterocycles |
Non-Patent Citations (2)
Title |
---|
右甲吗喃的合成工艺研究;田洪涛等;《今日药学》;20080815;第18卷(第04期);第63-64页 * |
赵知中.苄基衍生物.《有机化学中的保护基团》.科学出版社,1984,第58页. * |
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