DK141510B - Fremgangsmåde til fremstilling af N-acyldehydronortropinoner. - Google Patents
Fremgangsmåde til fremstilling af N-acyldehydronortropinoner. Download PDFInfo
- Publication number
- DK141510B DK141510B DK513574AA DK513574A DK141510B DK 141510 B DK141510 B DK 141510B DK 513574A A DK513574A A DK 513574AA DK 513574 A DK513574 A DK 513574A DK 141510 B DK141510 B DK 141510B
- Authority
- DK
- Denmark
- Prior art keywords
- reaction
- preparation
- mixture
- mmol
- ethyl acetate
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 14
- 238000002360 preparation method Methods 0.000 title description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- -1 phenyloxy Chemical group 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229930013930 alkaloid Natural products 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 4
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- XMLNCADGRIEXPK-KUMOIWDRSA-M chembl2146143 Chemical compound [Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C)C(=O)C(CO)C1=CC=CC=C1 XMLNCADGRIEXPK-KUMOIWDRSA-M 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- WQZLUKNOWXXMFL-UHFFFAOYSA-N 1,1,1,3-tetrabromopropan-2-one Chemical compound BrCC(=O)C(Br)(Br)Br WQZLUKNOWXXMFL-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 2
- 229910007565 Zn—Cu Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229940087654 iron carbonyl Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- FMDLEUPBHMCPQV-UHFFFAOYSA-N oct-2-en-4-one Chemical compound CCCCC(=O)C=CC FMDLEUPBHMCPQV-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- SAMNBOHOBWEEEU-UHFFFAOYSA-N tetrabromoacetone Natural products BrC(Br)C(=O)C(Br)Br SAMNBOHOBWEEEU-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QWVUOVZJBNQSNS-UHFFFAOYSA-N (+-)-Tropan-3endo,6exo-diol Natural products C1C(O)CC2C(O)CC1N2C QWVUOVZJBNQSNS-UHFFFAOYSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- UOPIOAUZQKSZRO-UHFFFAOYSA-N 2,4-dibromopentan-3-one Chemical compound CC(Br)C(=O)C(C)Br UOPIOAUZQKSZRO-UHFFFAOYSA-N 0.000 description 1
- OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
- UXWWXOPFZBZFAF-UHFFFAOYSA-N 5-(1-hydroxypropan-2-yl)cyclohexa-2,4-dien-1-one Chemical compound OCC(C)C1=CC=CC(=O)C1 UXWWXOPFZBZFAF-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000006957 Michael reaction Methods 0.000 description 1
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 1
- XQJMXPAEFMWDOZ-PBWFPOADSA-N [(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] benzoate Chemical compound C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-PBWFPOADSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- SLOCIJOTBVAMAJ-UHFFFAOYSA-N cycloheptane-1,2-dione Chemical compound O=C1CCCCCC1=O SLOCIJOTBVAMAJ-UHFFFAOYSA-N 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical class [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- FDYRAGSMOMPAMP-UHFFFAOYSA-M potassium sodium hydrogen carbonate nitrate Chemical class [N+](=O)([O-])[O-].[K+].C([O-])(O)=O.[Na+] FDYRAGSMOMPAMP-UHFFFAOYSA-M 0.000 description 1
- HUTQCVDTAWOOAV-UHFFFAOYSA-L potassium sodium nitric acid carbonate Chemical compound C([O-])([O-])=O.[Na+].[N+](=O)(O)[O-].[K+] HUTQCVDTAWOOAV-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- FIMXSEMBHGTNKT-UPGAHCIJSA-N scopine Chemical compound C([C@@H]1N2C)C(O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-UPGAHCIJSA-N 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11542473 | 1973-10-15 | ||
JP48115424A JPS5235680B2 (is") | 1973-10-15 | 1973-10-15 |
Publications (3)
Publication Number | Publication Date |
---|---|
DK513574A DK513574A (is") | 1975-06-16 |
DK141510B true DK141510B (da) | 1980-04-08 |
DK141510C DK141510C (is") | 1980-10-06 |
Family
ID=14662215
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK513574AA DK141510B (da) | 1973-10-15 | 1974-09-30 | Fremgangsmåde til fremstilling af N-acyldehydronortropinoner. |
Country Status (13)
Country | Link |
---|---|
US (1) | US4001249A (is") |
JP (1) | JPS5235680B2 (is") |
BE (1) | BE820588A (is") |
CA (1) | CA1048504A (is") |
CH (1) | CH605935A5 (is") |
DE (1) | DE2447978C2 (is") |
DK (1) | DK141510B (is") |
FR (1) | FR2247462B1 (is") |
GB (1) | GB1459908A (is") |
HU (1) | HU176008B (is") |
NL (1) | NL161756C (is") |
PL (1) | PL92979B1 (is") |
SE (1) | SE417317B (is") |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4472253A (en) * | 1981-08-17 | 1984-09-18 | The Florida Board Of Regents On Behalf Of The Florida State University | Process for the preparation of an N-substituted 3-O-alkyl-14-hydroxynormorphinone derivative |
FR2630439A1 (fr) * | 1988-04-22 | 1989-10-27 | Agronomique Inst Nat Rech | Composes chimiques et isomeres, leur preparation et leur utilisation pour la selection de microorganismes, procede pour cette selection et produit utilise |
US20040030199A1 (en) * | 2002-01-29 | 2004-02-12 | Maughon Robert R. | Process for reducing alpha-haloketones to secondary alpha-haloalcohols |
US20120271046A1 (en) | 2011-04-19 | 2012-10-25 | Jeffrey Christopher S | Nitrogen-containing heterocyclic compounds and methods of making the same |
CN102495170A (zh) * | 2011-11-26 | 2012-06-13 | 山东齐都药业有限公司 | 盐酸托烷司琼注射液中α-托品醇的检测方法 |
US11739084B2 (en) | 2021-10-07 | 2023-08-29 | Southwest Research Institute | Synthetic route to scopolamine and/or atropine |
KR20250054811A (ko) | 2022-08-26 | 2025-04-23 | 에이엠 케미칼스 엘엘씨 | 올리고뉴클레오티드 합성을 위한 범용 고체 지지체 및 포스포르아미다이트 빌딩 블록 |
-
1973
- 1973-10-15 JP JP48115424A patent/JPS5235680B2/ja not_active Expired
-
1974
- 1974-08-12 GB GB3551074A patent/GB1459908A/en not_active Expired
- 1974-08-12 US US05/496,579 patent/US4001249A/en not_active Expired - Lifetime
- 1974-09-30 DK DK513574AA patent/DK141510B/da unknown
- 1974-10-01 BE BE149115A patent/BE820588A/xx unknown
- 1974-10-08 DE DE2447978A patent/DE2447978C2/de not_active Expired
- 1974-10-08 CH CH1352674A patent/CH605935A5/xx not_active IP Right Cessation
- 1974-10-08 CA CA74210940A patent/CA1048504A/en not_active Expired
- 1974-10-10 NL NL7413372.A patent/NL161756C/xx not_active IP Right Cessation
- 1974-10-11 FR FR7434233A patent/FR2247462B1/fr not_active Expired
- 1974-10-11 PL PL1974174761A patent/PL92979B1/pl unknown
- 1974-10-14 SE SE7412919A patent/SE417317B/xx unknown
- 1974-10-14 HU HU74SA2701A patent/HU176008B/hu unknown
Also Published As
Publication number | Publication date |
---|---|
HU176008B (en) | 1980-11-28 |
BE820588A (fr) | 1975-02-03 |
GB1459908A (en) | 1976-12-31 |
FR2247462A1 (is") | 1975-05-09 |
US4001249A (en) | 1977-01-04 |
SE417317B (sv) | 1981-03-09 |
JPS5082091A (is") | 1975-07-03 |
PL92979B1 (is") | 1977-04-30 |
NL161756C (nl) | 1980-03-17 |
DE2447978A1 (de) | 1975-04-17 |
FR2247462B1 (is") | 1978-07-07 |
CH605935A5 (is") | 1978-10-13 |
DK513574A (is") | 1975-06-16 |
JPS5235680B2 (is") | 1977-09-10 |
DE2447978C2 (de) | 1982-11-04 |
CA1048504A (en) | 1979-02-13 |
SE7412919L (is") | 1975-04-16 |
DK141510C (is") | 1980-10-06 |
NL7413372A (nl) | 1975-04-17 |
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