CA2523419C - Process for preparation of (+)-p-mentha-2,8-diene-1-ol - Google Patents
Process for preparation of (+)-p-mentha-2,8-diene-1-ol Download PDFInfo
- Publication number
- CA2523419C CA2523419C CA2523419A CA2523419A CA2523419C CA 2523419 C CA2523419 C CA 2523419C CA 2523419 A CA2523419 A CA 2523419A CA 2523419 A CA2523419 A CA 2523419A CA 2523419 C CA2523419 C CA 2523419C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- amine
- alkyl
- process according
- oxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- MKPMHJQMNACGDI-UHFFFAOYSA-N 1-methyl-4-prop-1-en-2-ylcyclohex-2-en-1-ol Chemical compound CC(=C)C1CCC(C)(O)C=C1 MKPMHJQMNACGDI-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims description 43
- 238000002360 preparation method Methods 0.000 title description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 41
- 239000002841 Lewis acid Substances 0.000 claims abstract description 24
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 24
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 claims abstract description 14
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 12
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 12
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- -1 alkyl metal halide Chemical class 0.000 claims description 9
- 229910001507 metal halide Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 150000004820 halides Chemical group 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000013618 particulate matter Substances 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- 150000005309 metal halides Chemical class 0.000 claims 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 2
- 239000000543 intermediate Substances 0.000 abstract description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 150000002924 oxiranes Chemical group 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- 230000000707 stereoselective effect Effects 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
- 238000000197 pyrolysis Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- YTJVBLPAMBTDCH-RDBSUJKOSA-N (1s,2s,4r)-1-methyl-2-morpholin-4-yl-4-prop-1-en-2-ylcyclohexan-1-ol Chemical compound C1[C@H](C(=C)C)CC[C@](C)(O)[C@H]1N1CCOCC1 YTJVBLPAMBTDCH-RDBSUJKOSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 4
- 229940043279 diisopropylamine Drugs 0.000 description 4
- 229910013594 LiOAc Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229960004242 dronabinol Drugs 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229940087305 limonene Drugs 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CCEFMUBVSUDRLG-BBBLOLIVSA-N (+)-trans-limonene oxide Chemical compound C1[C@H](C(=C)C)CC[C@]2(C)O[C@@H]21 CCEFMUBVSUDRLG-BBBLOLIVSA-N 0.000 description 1
- FIBYEHQMESYELP-UJMBWUOASA-N (1S,2S,4R)-1-methyl-2-piperidin-1-yl-4-prop-1-en-2-ylcyclohexan-1-ol Chemical compound N1(CCCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C FIBYEHQMESYELP-UJMBWUOASA-N 0.000 description 1
- 229930007447 (4R)-limonene 1alpha,2alpha-epoxide Natural products 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000006728 Cope elimination reaction Methods 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- NLEIDZBFXWJTHY-DAVHSNPESA-N N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C Chemical compound N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C NLEIDZBFXWJTHY-DAVHSNPESA-N 0.000 description 1
- HWXUNMHJUXBUPR-DAVHSNPESA-N N1(CCOCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCOCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C Chemical compound N1(CCOCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C.N1(CCOCC1)[C@@H]1[C@](CC[C@H](C1)C(=C)C)(O)C HWXUNMHJUXBUPR-DAVHSNPESA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
- C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
- C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46504603P | 2003-04-24 | 2003-04-24 | |
| US60/465,046 | 2003-04-24 | ||
| PCT/US2004/011509 WO2004096740A2 (en) | 2003-04-24 | 2004-04-14 | Process for preparation of (+)-p-mentha-2,8-diene-1-ol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2523419A1 CA2523419A1 (en) | 2004-11-11 |
| CA2523419C true CA2523419C (en) | 2012-05-01 |
Family
ID=33418173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2523419A Expired - Fee Related CA2523419C (en) | 2003-04-24 | 2004-04-14 | Process for preparation of (+)-p-mentha-2,8-diene-1-ol |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7323607B2 (enExample) |
| EP (1) | EP1660421A2 (enExample) |
| JP (1) | JP2006524247A (enExample) |
| CN (1) | CN1777569A (enExample) |
| AU (1) | AU2004234350A1 (enExample) |
| CA (1) | CA2523419C (enExample) |
| MX (1) | MXPA05011292A (enExample) |
| WO (1) | WO2004096740A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009536623A (ja) | 2006-04-24 | 2009-10-15 | アラーガン、インコーポレイテッド | 眼圧降下剤としてのアブノーマル・カンナビジオール化合物 |
| CN112661656B (zh) * | 2020-12-19 | 2022-05-20 | 浙江新和成股份有限公司 | (1s,4r)-1-甲基-4-(1-甲基乙烯基)-2-环己烯-1-醇的制备方法 |
| US11739050B2 (en) * | 2021-09-07 | 2023-08-29 | Sci Pharmtech Inc. | Method for purification of terpenoid amino alcohol derivatives |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538164A (en) * | 1968-02-08 | 1970-11-03 | Reynolds Tobacco Co R | Synthesis of dihydrocarvone |
| US3814733A (en) * | 1970-07-27 | 1974-06-04 | Smc Corp | Isomerization of(+)-trans-2,3-epoxy-ciscarane to(+)-cis-2,8-p-methadiene-1-ol |
| US3734930A (en) * | 1971-09-22 | 1973-05-22 | R Razdan | Direct synthesis of ({31 )-trans-{66 {11 tetrahydrocannabinol from olivetol and ({30 )-trans-{66 {11 -carene oxide |
| US4025516A (en) * | 1975-06-23 | 1977-05-24 | The John C. Sheehan Institute For Research, Inc. | Process for the preparation of (-)-6a,10a-trans-6a,7,8,10a-tetrahydrodibenzo[b,d]-pyrans |
| IL48824A (en) * | 1976-01-12 | 1980-05-30 | Yissum Res Dev Co | Pharmaceutical compositions containing (3s,js) tetrahydrocanabinol derivatives and some novel compounds of this type |
| US4296257A (en) * | 1980-01-07 | 1981-10-20 | Scm Corporation | Process for producing dihydrocarvone geometric isomers |
| CH646933A5 (fr) * | 1981-05-04 | 1984-12-28 | Firmenich & Cie | Procede pour la preparation de (+)-p-mentha-2,8-diene-1-ol. |
| US6262278B1 (en) * | 1995-03-14 | 2001-07-17 | President And Fellows Of Harvard College | Stereoselective ring opening reactions |
| US5777137A (en) * | 1995-11-01 | 1998-07-07 | University Of Florida | Pancratistatins and processes for their production |
-
2004
- 2004-04-14 CA CA2523419A patent/CA2523419C/en not_active Expired - Fee Related
- 2004-04-14 AU AU2004234350A patent/AU2004234350A1/en not_active Abandoned
- 2004-04-14 EP EP04760258A patent/EP1660421A2/en not_active Withdrawn
- 2004-04-14 CN CNA2004800109761A patent/CN1777569A/zh active Pending
- 2004-04-14 US US10/549,976 patent/US7323607B2/en not_active Expired - Lifetime
- 2004-04-14 MX MXPA05011292A patent/MXPA05011292A/es active IP Right Grant
- 2004-04-14 WO PCT/US2004/011509 patent/WO2004096740A2/en not_active Ceased
- 2004-04-14 JP JP2006510032A patent/JP2006524247A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN1777569A (zh) | 2006-05-24 |
| CA2523419A1 (en) | 2004-11-11 |
| US7323607B2 (en) | 2008-01-29 |
| WO2004096740A2 (en) | 2004-11-11 |
| EP1660421A2 (en) | 2006-05-31 |
| MXPA05011292A (es) | 2006-01-24 |
| US20060084828A1 (en) | 2006-04-20 |
| WO2004096740A3 (en) | 2005-06-02 |
| JP2006524247A (ja) | 2006-10-26 |
| AU2004234350A1 (en) | 2004-11-11 |
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