CN110818578A - Catalytic hydrogenation synthesis method of chiral aminobutanol - Google Patents
Catalytic hydrogenation synthesis method of chiral aminobutanol Download PDFInfo
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- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 22
- 238000001308 synthesis method Methods 0.000 title claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 229910000510 noble metal Inorganic materials 0.000 claims abstract description 20
- 239000002798 polar solvent Substances 0.000 claims abstract description 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229940124277 aminobutyric acid Drugs 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000000706 filtrate Substances 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003495 polar organic solvent Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000005070 sampling Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 4
- OQEBBZSWEGYTPG-GSVOUGTGSA-N (3r)-3-aminobutanoic acid Chemical compound C[C@@H](N)CC(O)=O OQEBBZSWEGYTPG-GSVOUGTGSA-N 0.000 claims description 2
- OQEBBZSWEGYTPG-VKHMYHEASA-N (3s)-3-aminobutanoic acid Chemical compound C[C@H](N)CC(O)=O OQEBBZSWEGYTPG-VKHMYHEASA-N 0.000 claims description 2
- QWCKQJZIFLGMSD-GSVOUGTGSA-N D-alpha-aminobutyric acid Chemical compound CC[C@@H](N)C(O)=O QWCKQJZIFLGMSD-GSVOUGTGSA-N 0.000 claims description 2
- QWCKQJZIFLGMSD-VKHMYHEASA-N L-alpha-aminobutyric acid Chemical compound CC[C@H](N)C(O)=O QWCKQJZIFLGMSD-VKHMYHEASA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 3
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- JCBPETKZIGVZRE-BYPYZUCNSA-N (2s)-2-aminobutan-1-ol Chemical compound CC[C@H](N)CO JCBPETKZIGVZRE-BYPYZUCNSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 4
- 229960001618 ethambutol hydrochloride Drugs 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- AGMZSYQMSHMXLT-SCSAIBSYSA-N (3r)-3-aminobutan-1-ol Chemical compound C[C@@H](N)CCO AGMZSYQMSHMXLT-SCSAIBSYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 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
- 229960002542 dolutegravir Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- JCBPETKZIGVZRE-SCSAIBSYSA-N (2r)-2-aminobutan-1-ol Chemical compound CC[C@@H](N)CO JCBPETKZIGVZRE-SCSAIBSYSA-N 0.000 description 1
- AGMZSYQMSHMXLT-BYPYZUCNSA-N (3s)-3-aminobutan-1-ol Chemical compound C[C@H](N)CCO AGMZSYQMSHMXLT-BYPYZUCNSA-N 0.000 description 1
- 229940124321 AIDS medicine Drugs 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- 108010061833 Integrases Proteins 0.000 description 1
- 206010043275 Teratogenicity Diseases 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000000798 anti-retroviral effect Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229940072185 drug for treatment of tuberculosis Drugs 0.000 description 1
- 201000006674 extrapulmonary tuberculosis Diseases 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 231100000025 genetic toxicology Toxicity 0.000 description 1
- 230000001738 genotoxic effect Effects 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
Classifications
-
- 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
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- 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
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a catalytic hydrogenation synthesis method of chiral aminobutanol, which directly obtains the chiral aminobutanol by taking chiral aminobutyric acid as a raw material and performing catalytic hydrogenation by using a noble metal catalyst in the presence of protonic acid and a polar solvent. According to the invention, a noble metal catalyst is used as a reducing agent, the catalyst can be recycled, and the chiral aminobutyric acid is completely reduced into the chiral aminobutanol by reacting in a polar solvent system, so that the aminobutanol with high purity and high optical purity is synthesized.
Description
Technical Field
The invention belongs to the technical field of synthesis of medical intermediates, and particularly relates to a synthesis method of chiral aminobutanol.
Background
The (S) -2-aminobutanol is an important intermediate for synthesizing ethambutol hydrochloride which is an antituberculosis drug, and the ethambutol hydrochloride has obvious curative effect on various tuberculosis which is popular at present, including pulmonary tuberculosis and extrapulmonary tuberculosis. The medicament has the obvious characteristics of remarkable medicinal effect, treatment effect on tuberculosis without effect of other medicaments, stronger selective inhibition effect on tubercle bacillus and no drug resistance of tubercle bacillus in a patient to other medicaments.
(R) -3-aminobutanol is an important intermediate for synthesizing new anti-HIV/AIDS drug Lutelvir. Dolutegravir is a human immunodeficiency virus type 1(HIV1) integrase chain transfer inhibitor (INSTI), is used for treating HIV1 infection together with other antiretroviral drugs, and clinical research results show that the dolutegravir is low in toxicity, free of genotoxicity and carcinogenic toxicity, free of obvious fertility toxicity and teratogenicity toxicity when the clinical dosage is 27 times larger than the clinical dosage, strong in HIV1 virus resistance activity is shown by in vitro and in vivo test researches, and safety and tolerance are good.
Various overseas research institutions and enterprises have a certain degree of research on the synthesis of ethambutol hydrochloride, but have strict patent protection, while at present, the domestic research is less, and the domestic demand for the medicine is mainly met by import; therefore, the research on the synthesis process of ethambutol hydrochloride finds a synthesis route which has lower cost and simpler steps, can meet the industrial requirements, and is very important for developing a new process for autonomously synthesizing the medicine in China.
Disclosure of Invention
In view of the above, the main objective of the present invention is to provide a catalytic hydrogenation synthesis method of chiral aminobutanol.
In order to achieve the purpose, the technical scheme of the invention is realized as follows:
chiral aminobutyric acid is used as a raw material, and is directly subjected to catalytic hydrogenation by a noble metal catalyst in the presence of protonic acid and a polar solvent to obtain chiral aminobutanol.
Compared with the prior art, the invention adopts the noble metal catalyst as the reducing agent, the catalyst can be recycled and reacted in a polar solvent system, and the chiral aminobutyric acid is completely reduced into the chiral aminobutanol, thereby synthesizing the aminobutanol with high purity and high optical purity.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The embodiment of the invention provides a catalytic hydrogenation synthesis method of chiral aminobutanol, which directly obtains the chiral aminobutanol by taking chiral aminobutanoic acid as a raw material and performing catalytic hydrogenation by using a noble metal catalyst in the presence of protonic acid and a polar solvent.
Specifically, chiral aminobutyric acid, a noble metal catalyst, protonic acid and a polar solvent are added into a hydrogenation reaction kettle in batches, the mixture is heated to 50-150 ℃, the pressure is kept at 1.0-10 MPa, the mixture is sampled and analyzed after 2-10 hours, after the reaction is determined, the noble metal catalyst is filtered, filtrate is collected, 1.5 eq-5.5 eq of solid sodium hydroxide is added into the filtrate, 1V-5V of the polar organic solvent is added, the mixture is stirred, stood and layered, the lower layer is continuously and repeatedly extracted, the upper layer is collected, the operation is repeated for three times, the collected upper layer organic phase is firstly distilled to remove the polar organic solvent, and the chiral aminobutanol is obtained through reduced pressure distillation.
The mass ratio of the chiral aminobutyric acid to the noble metal catalyst to the polar solvent is 1: (0.05-0.5): (1-20).
The chiral aminobutyric acid is one or a mixture of at least two of (R) -2-aminobutyric acid, (R) -3-aminobutyric acid, (R) -4-aminobutyric acid, (S) -2-aminobutyric acid, (S) -3-aminobutyric acid and (S) -4-aminobutyric acid.
The protonic acid is one or a mixture of at least two of phosphoric acid, sulfuric acid, hydrochloric acid, trifluoroacetic acid and the like.
The polar solvent is one or a mixture of at least two of methanol, ethanol, isopropanol and water.
The noble metal catalyst is a ruthenium-or rhodium-based catalyst.
Example 1
The embodiment 1 of the invention provides a catalytic hydrogenation synthesis method of (S) -2-aminobutanol, which comprises the steps of adding 70 g of (S) -2-aminobutanol, 400 g of water and 220g of sulfuric acid into a 1L hydrogenation reaction kettle in batches, heating to 95-100 ℃, keeping the pressure at 5Mpa for 10 hours, then sampling and analyzing, after the reaction is finished, filtering a noble metal catalyst, collecting filtrate, adding 40g of solid sodium hydroxide into the filtrate, adding 140ml of anhydrous methanol, stirring, standing, layering, continuously and repeatedly extracting the lower layer, collecting the upper layer, repeating the operation for three times, distilling the collected upper layer organic phase to remove a polar organic solvent, and then carrying out reduced pressure distillation to obtain the chiral aminobutanol with higher purity.
The purity of the aminobutanol synthesized in example 1 of the present invention was 99%, the mass was 54.4g, and the molar yield was 90%.
Example 2
The embodiment 2 of the invention provides a catalytic hydrogenation synthesis method of (S) -3-aminobutanol, which comprises the steps of adding 70 g of (S) -2-aminobutanol, 400 g of water and 220g of sulfuric acid into a 1L hydrogenation reaction kettle in batches, heating to 95-100 ℃, keeping the pressure at 5Mpa for 10 hours, then sampling and analyzing, after the reaction is finished, filtering a noble metal catalyst, collecting filtrate, adding 40g of solid sodium hydroxide into the filtrate, adding 140ml of anhydrous methanol, stirring, standing, layering, continuously and repeatedly extracting the lower layer, collecting the upper layer, repeating the operation for three times, distilling the collected upper layer organic phase to remove a polar organic solvent, and then carrying out reduced pressure distillation to obtain the chiral aminobutanol with higher purity.
The chromatographic purity of the aminobutanol synthesized in the example 2 of the invention is 99%, the mass is 55g, and the molar yield is 91%.
Example 3
The embodiment 3 of the invention provides a catalytic hydrogenation synthesis method of (S) -4-aminobutanol, which comprises the steps of adding 70 g of (S) -2-aminobutanol, 400 g of water and 220g of sulfuric acid into a 1L hydrogenation reaction kettle in batches, heating to 95-100 ℃, keeping the pressure at 5Mpa for 10 hours, then sampling and analyzing, after the reaction is finished, filtering a noble metal catalyst, collecting filtrate, adding 40g of solid sodium hydroxide into the filtrate, adding 140ml of anhydrous methanol, stirring, standing, layering, continuously and repeatedly extracting the lower layer, collecting the upper layer, repeating the operation for three times, distilling the collected upper layer organic phase to remove a polar organic solvent, and then carrying out reduced pressure distillation to obtain the chiral aminobutanol with higher purity.
The purity of the aminobutanol synthesized in example 3 of the present invention was 99%, and the molar yield was 89.4% or more, when the mass was 54 g.
Example 4
The embodiment 4 of the invention provides a catalytic hydrogenation synthesis method of (R) -2-aminobutanol, which comprises the steps of adding 70 g of (S) -2-aminobutanol, 400 g of water and 220g of phosphoric acid into a 1L hydrogenation reaction kettle in batches, heating to 95-100 ℃, keeping the pressure at 5Mpa for 10 hours, then sampling and analyzing, after the reaction is finished, filtering a noble metal catalyst, collecting filtrate, adding 80g of solid sodium hydroxide into the filtrate, adding 140ml of anhydrous methanol, stirring, standing, layering, continuously and repeatedly extracting the lower layer, collecting the upper layer, repeating the operation for three times, distilling the collected upper layer organic phase to remove a polar organic solvent, and then carrying out reduced pressure distillation to obtain the chiral aminobutanol with higher purity.
The purity of the aminobutanol synthesized in example 4 of the present invention was 99%, the mass was 54.4g, and the molar yield was 90%.
Example 5
The embodiment 5 of the invention provides a catalytic hydrogenation synthesis method of (R) -3-aminobutanol, which comprises the steps of adding 70 g of (S) -2-aminobutanol, 400 g of water and 220g of phosphoric acid into a 1L hydrogenation reaction kettle in batches, heating to 95-100 ℃, keeping the pressure at 5Mpa for 10 hours, then sampling and analyzing, filtering a noble metal catalyst after the reaction is finished, collecting filtrate, adding 80g of solid sodium hydroxide into the filtrate, adding 140ml of anhydrous methanol, stirring, standing, layering, continuously and repeatedly extracting the lower layer, collecting the upper layer, repeating the operation for three times, distilling the collected upper layer organic phase to remove a polar organic solvent, and carrying out reduced pressure distillation to obtain the chiral aminobutanol with higher purity.
The purity of the aminobutanol synthesized in example 5 of the present invention was 99%, the mass was 55g, and the molar yield was 91%.
Example 6
The embodiment 6 of the invention provides a catalytic hydrogenation synthesis method of (R) -4-aminobutanol, which comprises the steps of adding 70 g of (S) -2-aminobutanol, 400 g of water and 220g of phosphoric acid into a 1L hydrogenation reaction kettle in batches, heating to 95-100 ℃, keeping the pressure at 5Mpa for 10 hours, then sampling and analyzing, after the reaction is finished, filtering a noble metal catalyst, collecting filtrate, adding 80g of solid sodium hydroxide into the filtrate, adding 140ml of anhydrous methanol, stirring, standing, layering, continuously and repeatedly extracting the lower layer, collecting the upper layer, repeating the operation for three times, distilling the collected upper layer organic phase to remove a polar organic solvent, and then carrying out reduced pressure distillation to obtain the chiral aminobutanol with higher purity.
The amino butanol synthesized in example 6 of the present invention had an optical purity of 99%, a mass of 54g, and a molar yield of 89.4%.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the scope of the present invention.
Claims (7)
1. A catalytic hydrogenation synthesis method of chiral aminobutanol is characterized in that: chiral aminobutyric acid is used as a raw material, and is directly subjected to catalytic hydrogenation by a noble metal catalyst in the presence of protonic acid and a polar solvent to obtain chiral aminobutanol.
2. The catalytic hydrogenation synthesis method of chiral aminobutanol according to claim 1, characterized in that chiral aminobutyric acid, noble metal catalyst, protonic acid and polar solvent are added into a hydrogenation reaction kettle in batches, the mixture is heated to 50-150 ℃ and kept at 1.0-10 Mpa, sampling analysis is carried out after 2-10 hours, after the reaction is determined, the noble metal catalyst is filtered, filtrate is collected, 1.5 eq-5.5 eq of solid sodium hydroxide is added into the filtrate, 1V-5V of polar organic solvent is added, stirring, standing and layering are carried out, the lower layer is continuously extracted repeatedly, the upper layer is collected and repeated for three times, the collected upper layer organic phase is distilled to remove the polar organic solvent, and the chiral aminobutanol is obtained through reduced pressure distillation.
3. The catalytic hydrogenation synthesis method of chiral aminobutanol according to claim 1 or 2, wherein the mass ratio of the chiral aminobutanol to the noble metal catalyst to the polar solvent is 1: (0.05-0.5): (1-20).
4. The catalytic hydrogenation synthesis method of chiral amino butanol according to claim 3, wherein the chiral amino butyric acid is one or a mixture of at least two of (R) -2-aminobutyric acid, (R) -3-aminobutyric acid, (R) -4-aminobutyric acid, (S) -2-aminobutyric acid, (S) -3-aminobutyric acid, (S) -4-aminobutyric acid).
5. The catalytic hydrogenation synthesis method of chiral amino butanol according to claim 4, wherein the protonic acid is a mixture of at least two of phosphoric acid, sulfuric acid, hydrochloric acid, trifluoroacetic acid, and the like.
6. The catalytic hydrogenation synthesis method of chiral amino butanol according to claim 5, wherein the polar solvent is a mixture of at least two of methanol, ethanol, isopropanol and water.
7. The catalytic hydrogenation synthesis method of chiral aminobutanol according to claim 6, characterized in that the noble metal catalyst is a ruthenium-or rhodium-based catalyst.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113336655A (en) * | 2020-12-30 | 2021-09-03 | 江西迪赛诺制药有限公司 | Preparation method of (R) -3-aminobutanol |
| CN114573463A (en) * | 2022-03-23 | 2022-06-03 | 江西宇能制药股份有限公司 | Preparation method of R-3-aminobutanol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113336655A (en) * | 2020-12-30 | 2021-09-03 | 江西迪赛诺制药有限公司 | Preparation method of (R) -3-aminobutanol |
| CN114573463A (en) * | 2022-03-23 | 2022-06-03 | 江西宇能制药股份有限公司 | Preparation method of R-3-aminobutanol |
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