JPWO2022014414A5 - - Google Patents
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- Publication number
- JPWO2022014414A5 JPWO2022014414A5 JP2022536280A JP2022536280A JPWO2022014414A5 JP WO2022014414 A5 JPWO2022014414 A5 JP WO2022014414A5 JP 2022536280 A JP2022536280 A JP 2022536280A JP 2022536280 A JP2022536280 A JP 2022536280A JP WO2022014414 A5 JPWO2022014414 A5 JP WO2022014414A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- optically active
- substituents
- carbon atom
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 150000004700 cobalt complex Chemical class 0.000 claims description 18
- KYWYAWFSWFSPAY-UHFFFAOYSA-N 1,1,3-trimethyl-2,3-dihydroinden-4-amine Chemical compound C1=CC(N)=C2C(C)CC(C)(C)C2=C1 KYWYAWFSWFSPAY-UHFFFAOYSA-N 0.000 claims description 17
- 150000004678 hydrides Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 239000003638 chemical reducing agent Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- -1 cobalt halide salt Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000005270 trialkylamine group Chemical group 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000010494 dissociation reaction Methods 0.000 claims description 2
- 230000005593 dissociations Effects 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KYWYAWFSWFSPAY-MRVPVSSYSA-N (3r)-1,1,3-trimethyl-2,3-dihydroinden-4-amine Chemical compound C1=CC(N)=C2[C@H](C)CC(C)(C)C2=C1 KYWYAWFSWFSPAY-MRVPVSSYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020122762 | 2020-07-17 | ||
| JP2020122762 | 2020-07-17 | ||
| PCT/JP2021/025489 WO2022014414A1 (ja) | 2020-07-17 | 2021-07-06 | 光学活性な化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2022014414A1 JPWO2022014414A1 (enExample) | 2022-01-20 |
| JPWO2022014414A5 true JPWO2022014414A5 (enExample) | 2024-07-08 |
| JP7662640B2 JP7662640B2 (ja) | 2025-04-15 |
Family
ID=79554611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022536280A Active JP7662640B2 (ja) | 2020-07-17 | 2021-07-06 | 光学活性な化合物の製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20230257408A1 (enExample) |
| EP (1) | EP4186882A4 (enExample) |
| JP (1) | JP7662640B2 (enExample) |
| KR (1) | KR20230041010A (enExample) |
| CN (1) | CN115836041B (enExample) |
| AU (1) | AU2021308138A1 (enExample) |
| BR (1) | BR112022026601A2 (enExample) |
| CA (1) | CA3186051A1 (enExample) |
| IL (1) | IL299590B1 (enExample) |
| WO (1) | WO2022014414A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114773263B (zh) * | 2022-05-16 | 2023-09-05 | 江苏百康德医药科技有限公司 | (r)-2,2,4-三甲基-1,2,3,4-四氢喹啉的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0654464A1 (en) * | 1993-10-22 | 1995-05-24 | Shell Internationale Researchmaatschappij B.V. | Processes for the preparation of pesticides and intermediates |
| US5521317A (en) | 1993-10-22 | 1996-05-28 | American Cyanamid Co. | Processes for the preparation of pesticides and intermediates |
| JP2012025735A (ja) * | 2010-06-24 | 2012-02-09 | Sumitomo Chemical Co Ltd | 植物病害防除組成物及び植物病害防除方法 |
| WO2013086397A1 (en) * | 2011-12-08 | 2013-06-13 | Array Biopharma Inc. | Urea compounds as gka activators |
| CN104619681A (zh) * | 2012-08-31 | 2015-05-13 | 住友化学株式会社 | (r)-1,1,3-三甲基-4-氨基茚满的制造方法 |
| CN105992755B (zh) | 2014-02-07 | 2018-07-13 | 住友化学株式会社 | (r)-1,1,3-三甲基-4-氨基茚满的制造方法 |
| DE112015001290T5 (de) * | 2014-03-18 | 2016-12-29 | Sumitomo Chemical Company, Limited | Verfahren zur Herstellung optisch aktiver Verbindungen |
| JP6780011B2 (ja) * | 2016-04-15 | 2020-11-04 | スティヒティング アイ−エフ プロダクト コラボレイション | ４−アミノインダン誘導体及び関連アミノインダンアミドの調製方法 |
| JP2018039757A (ja) * | 2016-09-08 | 2018-03-15 | 日産化学工業株式会社 | イミダゾール誘導体の製造方法 |
| CN110655456B (zh) * | 2019-09-16 | 2020-11-24 | 浙江大学 | 一种e/z混合或单一构型的三取代烯烃的不对称催化氢化制备手性烷基化合物的方法 |
-
2021
- 2021-07-06 KR KR1020237003992A patent/KR20230041010A/ko active Pending
- 2021-07-06 CA CA3186051A patent/CA3186051A1/en active Pending
- 2021-07-06 BR BR112022026601A patent/BR112022026601A2/pt unknown
- 2021-07-06 AU AU2021308138A patent/AU2021308138A1/en active Pending
- 2021-07-06 EP EP21842357.2A patent/EP4186882A4/en active Pending
- 2021-07-06 US US18/005,161 patent/US20230257408A1/en active Pending
- 2021-07-06 WO PCT/JP2021/025489 patent/WO2022014414A1/ja not_active Ceased
- 2021-07-06 CN CN202180049266.3A patent/CN115836041B/zh active Active
- 2021-07-06 JP JP2022536280A patent/JP7662640B2/ja active Active
-
2022
- 2022-12-29 IL IL299590A patent/IL299590B1/en unknown
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