CN104961640A - 一种光学纯的3-氨基-1-丁醇的制备方法 - Google Patents
一种光学纯的3-氨基-1-丁醇的制备方法 Download PDFInfo
- Publication number
- CN104961640A CN104961640A CN201510444447.2A CN201510444447A CN104961640A CN 104961640 A CN104961640 A CN 104961640A CN 201510444447 A CN201510444447 A CN 201510444447A CN 104961640 A CN104961640 A CN 104961640A
- Authority
- CN
- China
- Prior art keywords
- reaction
- preparation
- cymene
- binap
- benzoyl
- 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
Links
- 238000002360 preparation method Methods 0.000 title claims description 28
- AGMZSYQMSHMXLT-UHFFFAOYSA-N 3-aminobutan-1-ol Chemical compound CC(N)CCO AGMZSYQMSHMXLT-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 35
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 25
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003446 ligand Substances 0.000 claims abstract description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 claims abstract description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 16
- 229930007927 cymene Natural products 0.000 claims description 16
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 150000004702 methyl esters Chemical group 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- CHOLPKIHPFNIPE-UHFFFAOYSA-N phosphanylphosphane rhodium Chemical compound [Rh].PP CHOLPKIHPFNIPE-UHFFFAOYSA-N 0.000 abstract 1
- -1 3-amino-n-butyl Chemical group 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229960004756 ethanol Drugs 0.000 description 8
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 238000010189 synthetic method Methods 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 4
- 238000004904 shortening Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FYAOKMGCDCMVTC-UHFFFAOYSA-N CCC(C)C(=O)ONC(=O)C1=CC=CC=C1 Chemical compound CCC(C)C(=O)ONC(=O)C1=CC=CC=C1 FYAOKMGCDCMVTC-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007360 debenzoylation reaction Methods 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- RHWKPHLQXYSBKR-BMIGLBTASA-N dolutegravir Chemical compound C([C@@H]1OCC[C@H](N1C(=O)C1=C(O)C2=O)C)N1C=C2C(=O)NCC1=CC=C(F)C=C1F RHWKPHLQXYSBKR-BMIGLBTASA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- BGVLBVASHIQNIO-UHFFFAOYSA-N 1,4,8,11-tetrazacyclotetradecane-5,7-dione Chemical class O=C1CC(=O)NCCNCCCNCCN1 BGVLBVASHIQNIO-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- 229940124321 AIDS medicine Drugs 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229960002542 dolutegravir Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002961 penems Chemical class 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014075 tivicay Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510444447.2A CN104961640B (zh) | 2015-07-26 | 2015-07-26 | 一种光学纯的3-氨基-1-丁醇的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510444447.2A CN104961640B (zh) | 2015-07-26 | 2015-07-26 | 一种光学纯的3-氨基-1-丁醇的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104961640A true CN104961640A (zh) | 2015-10-07 |
CN104961640B CN104961640B (zh) | 2016-09-07 |
Family
ID=54215767
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510444447.2A Active CN104961640B (zh) | 2015-07-26 | 2015-07-26 | 一种光学纯的3-氨基-1-丁醇的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104961640B (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106748816A (zh) * | 2016-11-30 | 2017-05-31 | 河南师范大学 | 一种度鲁特韦关键中间体(r)‑3‑氨基丁醇的合成方法 |
CN107793320A (zh) * | 2016-09-05 | 2018-03-13 | 上海迪赛诺药业股份有限公司 | 手性拆分制备单一构型3‑氨基‑1‑丁醇的方法 |
CN107805205A (zh) * | 2017-11-10 | 2018-03-16 | 浙江新和成股份有限公司 | 一种(r)‑3‑氨基丁醇的制备方法 |
CN108586272A (zh) * | 2018-06-28 | 2018-09-28 | 浙江昌明药业有限公司 | 一种3-氨基丙醇或3-氨基丙酸衍生物的制备方法 |
CN109608344A (zh) * | 2018-12-28 | 2019-04-12 | 凯瑞斯德生化(苏州)有限公司 | 一种(r)-3-氨基丁醇的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104370755A (zh) * | 2014-08-18 | 2015-02-25 | 江西隆莱生物制药有限公司 | 一种光学活性的3-氨基丁醇和3-氨基丁酸的制备方法 |
-
2015
- 2015-07-26 CN CN201510444447.2A patent/CN104961640B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104370755A (zh) * | 2014-08-18 | 2015-02-25 | 江西隆莱生物制药有限公司 | 一种光学活性的3-氨基丁醇和3-氨基丁酸的制备方法 |
Non-Patent Citations (2)
Title |
---|
EZZAT RAFIEE ET AL.: "A revision for the synthesis of b-enaminones in solvent free conditions: efficacy of different supported heteropoly acids as active and reusable catalysts", 《GREEN CHEM.》 * |
李叶芝: "由氨基酸酯制备氨基醇", 《化学技术与开发》 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107793320A (zh) * | 2016-09-05 | 2018-03-13 | 上海迪赛诺药业股份有限公司 | 手性拆分制备单一构型3‑氨基‑1‑丁醇的方法 |
CN107793320B (zh) * | 2016-09-05 | 2022-06-28 | 上海迪赛诺药业股份有限公司 | 手性拆分制备单一构型3-氨基-1-丁醇的方法 |
CN106748816A (zh) * | 2016-11-30 | 2017-05-31 | 河南师范大学 | 一种度鲁特韦关键中间体(r)‑3‑氨基丁醇的合成方法 |
CN107805205A (zh) * | 2017-11-10 | 2018-03-16 | 浙江新和成股份有限公司 | 一种(r)‑3‑氨基丁醇的制备方法 |
CN107805205B (zh) * | 2017-11-10 | 2020-05-26 | 浙江新和成股份有限公司 | 一种(r)-3-氨基丁醇的制备方法 |
CN108586272A (zh) * | 2018-06-28 | 2018-09-28 | 浙江昌明药业有限公司 | 一种3-氨基丙醇或3-氨基丙酸衍生物的制备方法 |
CN109608344A (zh) * | 2018-12-28 | 2019-04-12 | 凯瑞斯德生化(苏州)有限公司 | 一种(r)-3-氨基丁醇的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN104961640B (zh) | 2016-09-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104961640A (zh) | 一种光学纯的3-氨基-1-丁醇的制备方法 | |
CN107805205B (zh) | 一种(r)-3-氨基丁醇的制备方法 | |
CN104370755B (zh) | 一种光学活性的3‑氨基丁醇和3‑氨基丁酸的制备方法 | |
CN104447445A (zh) | 一种合成阿普斯特中间体的制备方法 | |
CN105348172B (zh) | (s)‑1‑(4‑甲氧基‑3‑乙氧基)苯基‑2‑甲磺酰基乙胺的制备及阿普斯特的制备方法 | |
CN112047883B (zh) | 顺苯磺酸阿曲库铵的制备方法 | |
CN105001098A (zh) | 一种3(r)/(s)-氨基-1-丁醇的制备方法 | |
KR101292329B1 (ko) | 알킬락테이트의 제조방법 및 이를 이용한 락타미드의 제조방법 | |
WO2005044805A1 (fr) | Procede d'elaboration de donepezil et de ses derives | |
CN102766190B (zh) | 雷公藤内酯醇中间体不对称合成方法 | |
CN112645833A (zh) | 一种(s)-2,6-二氨基-5-氧己酸的合成方法 | |
CN110683960A (zh) | 一种(r)-3-氨基丁醇的合成方法 | |
CN108440349B (zh) | 一种手性光学纯对甲苯亚磺酰胺的制备方法 | |
CN114315609B (zh) | 一种制备顺式2-氨基环己醇的工艺方法 | |
CN101743218B (zh) | 光学活性反式-2-氨基环己醇的制备方法及其中间体 | |
CN109265385B (zh) | 一种手性催化剂的合成工艺 | |
CN101481335B (zh) | 卡巴拉汀中间体的制备方法 | |
CN101519351B (zh) | 一种高烯丙基醇酯的制备方法 | |
CN103788073A (zh) | 一种制备伏立康唑关键中间体的新方法 | |
CN108558714B (zh) | 一种手性光学纯对甲苯亚磺酰胺的制备方法 | |
CN109879775A (zh) | 一种5-氨基乙酰丙酸盐酸盐中间体的环保制备方法 | |
CN111807968A (zh) | 一种2-(1-环己烯基)乙胺的合成方法 | |
CN110396072A (zh) | (s)-3-羟基四氢呋喃的制备方法 | |
Wilken et al. | Enantioselective Catalytic Borane Reduction of Prochiral Ketones: Synthesis and Application of New Rigid β-Amino Alcohols with a Cycloalkanol Subunit | |
CN101723879A (zh) | 一种合成(r)-3-哌啶乙酸乙酯盐酸盐的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB02 | Change of applicant information |
Address after: 312455 Zhejiang city of Shengzhou Province Town Bridge Road No. 88 Applicant after: SHENGZHOU GREASE AND CHEMICAL Co.,Ltd. Address before: 312455 Zhejiang city of Quzhou province Shengzhou City Town Bridge Road No. 88 Applicant before: SHENGZHOU GREASE AND CHEMICAL Co.,Ltd. |
|
COR | Change of bibliographic data | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170111 Address after: 312455 Zhejiang city of Shengzhou Province Town Bridge Road No. 88 two floor Patentee after: Zhejiang Hong Kang Pharmaceutical Chemical Co.,Ltd. Address before: 312455 Zhejiang city of Shengzhou Province Town Bridge Road No. 88 Patentee before: SHENGZHOU GREASE AND CHEMICAL Co.,Ltd. |
|
PP01 | Preservation of patent right |
Effective date of registration: 20191025 Granted publication date: 20160907 |
|
PP01 | Preservation of patent right | ||
PD01 | Discharge of preservation of patent |
Date of cancellation: 20221025 Granted publication date: 20160907 |
|
PD01 | Discharge of preservation of patent |