CN114394976B - 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one - Google Patents
2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one Download PDFInfo
- Publication number
- CN114394976B CN114394976B CN202210127004.0A CN202210127004A CN114394976B CN 114394976 B CN114394976 B CN 114394976B CN 202210127004 A CN202210127004 A CN 202210127004A CN 114394976 B CN114394976 B CN 114394976B
- Authority
- CN
- China
- Prior art keywords
- solution
- azabicyclo
- oxa
- phenethyl
- micromixer
- 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.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1]Octane-7-one, synthesized by the following steps: step (1), dissolving the mixed solution of 3-butene-1-ol and alkali A and an activating reagentMixing the solutions in a micromixer, and flowing into a first reactor for reaction to obtain an intermediate I solution; step (2), the intermediate I solution is preparedS) Mixing 1-phenethylamine and alkali B solution in a micromixer, and flowing into a second reactor for reaction to obtain an intermediate II solution; and (3) mixing the intermediate II solution with glyoxylic acid or glyoxylic acid aqueous polymer solution in a micromixer, and flowing into a third reactor for reaction to obtain a target product. The intermediate steps of the process provided by the invention do not need separation and purification, the total yield is stabilized at 64-77%, in the process, the complicated operation flow is greatly simplified, the reaction time is greatly shortened, and the generation amount and variety of wastes are obviously reduced. Therefore, the synthesis process of the invention has the advantages of low cost, simple operation, high space-time efficiency, low discharge of three wastes, and the like.
Description
Technical Field
The invention relates to the field of chemical compositions, in particular to 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone.
Background
The structural formula of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one is shown below:
the compound can be used for preparing (2S, 4R) -4-hydroxy piperidine acid and derivatives thereof, and the (2S, 4R) -4-hydroxy piperidine acid can be used for preparing a second generation protease inhibitor palivir (Paritaaprevir), and in addition, the (2S, 4R) -4-hydroxy piperidine acid and derivatives thereof are hot spots of current research as pharmaceutical molecular building blocks.
The preparation route of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in the prior art: 3-butene-1-ol reacts with p-toluenesulfonyl chloride in the presence of triethylamine, nucleophilic substitution reaction is carried out with (S) -1-phenethylamine to obtain allylamine, and finally cyclisation with glyoxylate to obtain 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-one (J.org.chem.1996, 61, 2226-2231). The synthesis process of the 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone has the advantages of 60-72% of yield, long reaction time, more byproducts, complex process, low production efficiency, large amount of waste liquid generated in the post-treatment process and large amount of whole waste.
Disclosure of Invention
It is an object of the present invention to solve at least the above problems and to provide at least the advantages to be described later.
The invention aims to provide a green and efficient 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone synthesis process which is simple to operate and low in cost.
To achieve these objects and other advantages and in accordance with the purpose of the invention, there is provided a 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one synthesized by the steps of:
step (1), mixing a mixed solution of 3-butene-1-ol and alkali A and an activating reagent solution in a micromixer, and flowing into a first reactor for reaction to obtain an intermediate I solution;
step (2), mixing the intermediate I solution, (S) -1-phenethylamine and the alkali B solution in a micromixer, and flowing into a second reactor for reaction to obtain an intermediate II solution;
step (3), mixing the intermediate II solution with glyoxylic acid or glyoxylic acid aqueous solution in a micromixer, and flowing into a third reactor for reaction to obtain a target product 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone;
the chemical reaction process of the above synthetic method is as follows:
preferably, in the step (1), the activating reagent is sulfonyl halide or sulfonic anhydride; the base A is one or more of triethylamine, pyridine, substituted pyridine, diisopropylethylamine and 1, 8-diazabicyclo [5.4.0] undec-7-ene.
Preferably, the activating agent is methylsulfonic anhydride.
Preferably, in the step (1), 3-buten-1-ol: activating reagent: the molar ratio of the base A is 1.0: (1.0-1.5): (1.0-3.0), wherein the organic solvent is one or more of tetrahydrofuran, acetonitrile, dichloromethane, toluene, acetone, diethyl ether, chloroform, ethyl acetate, N-dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, dichloroethane and pyridine.
Preferably, in the step (1), the reaction temperature is 0-60 ℃, and the residence time of the reaction mixture is 1-30 minutes.
Preferably, in the step (2), the alkali B solution is one of pure organic alkali, an organic solution of organic alkali or an aqueous solution of inorganic alkali.
Preferably, the inorganic base is one or more of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, lithium bicarbonate, potassium bicarbonate and sodium bicarbonate; the organic base is one or more of triethylamine, pyridine, 2, 6-lutidine, 4-dimethylaminopyridine, diisopropylethylamine and 1, 8-diazabicyclo [5.4.0] undec-7-ene.
Preferably, in the step (2), the intermediate I solution: (S) -1-phenylethylamine: the mol ratio of the alkali B is 1 (1.0-1.5): (0-3.0), the reaction temperature is 60-260 ℃ and the reaction time is 10-100 minutes.
Preferably, in the step (3), the intermediate II solution: the mol ratio of glyoxylic acid or glyoxylic acid compound is 1 (1.0-3.0), the reaction temperature is 60-160 ℃, the reaction time is 10-100 minutes, and the back pressure of the back pressure valve is 1.0-3.0Mpa.
Preferably, the reactor in the steps (1) - (3) is any one of a microchannel reactor, a serial coil reactor and a tubular reactor, and the micromixer in the steps (1) - (3) is any one of a T-shaped micromixer, a Y-shaped micromixer, a multi-interaction thin-layer micromixer, a static micromixer, a chaotic micromixer and a dynamic micromixer.
The invention at least comprises the following beneficial effects:
1. the synthesis of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone is realized, the intermediate is not required to be separated and purified, the final product can be directly obtained, and the total yield is stabilized at 64-77%;
2. in the process, complicated operation procedures are greatly simplified, the reaction time is greatly shortened, and the generation amount and types of wastes are obviously reduced, so that the 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-one synthesis process provided by the invention has the advantages of low cost, simplicity and convenience in operation, high space-time efficiency, low emission of three wastes and the like.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a synthetic route diagram of the method of the present invention.
Detailed Description
The present invention is described in further detail below with reference to the drawings to enable those skilled in the art to practice the invention by referring to the description.
It will be understood that terms, such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
Example 1
The synthetic route of the 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone is shown in figure 1, an acetonitrile mixed solution of 3-butene-1-ol and triethylamine (alkali A) is respectively conveyed into a T-shaped micromixer through a pump A and a pump B to be mixed with an acetonitrile solution of methylsulfonic anhydride, and the mixed materials are then fed into a series coil reactor, wherein the total volume of the reactor is 8mL, and the reaction temperature is 30 ℃.
The raw material concentration and the flow rate of a feed pump are regulated, the mol ratio of 3-butene-1 alcohol, methylsulfonic anhydride and triethylamine (alkali A) is 1:1.1:1.2, the reaction is carried out for 5 minutes (namely the residence time of the mixed reaction materials in a reactor), the reaction solution is mixed with an acetonitrile solution of (S) -1-phenethylamine (pumped by a pump C) and an acetonitrile solution of triethylamine (alkali B) (pumped by a pump D) in a T-shaped micromixer, the mixed materials then enter a series coil reactor, the total volume of the reactor is 16mL, the reaction temperature is 200 ℃, the solution concentration and the flow rate of the feed pump are regulated, the mol ratio of 3-butene-1 alcohol, (S) -1-phenethylamine and triethylamine (alkali B) is 1:1.1:1.2, the reaction is carried out for 16 minutes, and the reaction solution and the acetonitrile solution of glyoxylic acid (pumped by a pump E) are mixed in the T-shaped micromixer.
The mixture was then fed into a series coil reactor, the total volume of the reactor was 16mL, the reaction temperature was 120 ℃, and the glyoxylate concentration and feed pump flow rate were adjusted to 3-buten-1-ol: the molar ratio of glyoxylic acid is 1:1.5, the reaction is carried out for 30 minutes, the back pressure of a back pressure valve is 2.0Mpa, and an acetonitrile solution of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone is obtained after a period of time.
The reaction process is as follows:
the obtained 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-one solution was concentrated, saturated brine was added, the pH was adjusted to 8 to 9 with sodium carbonate, extraction was performed with ethyl acetate, the organic phase was washed with saturated sodium bicarbonate solution, saturated brine was washed, dried over anhydrous sodium sulfate and then filtered, and distillation was performed under reduced pressure to obtain 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-one in a yield of 76%.
Example 2
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, 3-butene-1-ol and diisopropylethylamine (base A) were fed in acetonitrile by pump A, the concentration of the raw materials and the flow rate of the feed pump were adjusted so that the molar ratio of 3-butene-1-ol, methylsulfonic anhydride and diisopropylethylamine was 1:1.5:2.2, the reaction temperature in the first step was 0℃and the reaction time was 30 minutes, and the product 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-one obtained in this example was produced in 74% yield.
Example 3
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in the embodiment, the pump A is fed with a mixture of 3-butene-1-ol and triethylamine, and no solvent is added; the raw material concentration and the flow rate of a feed pump are regulated to ensure that the mol ratio of 3-butene-1-1, methanesulfonic anhydride and triethylamine (alkali A) is 1:1.0:3.0, and the reaction temperature of the first step is 60 ℃ and the reaction time is 1 minute. The pump D is not used, the alkali B is not needed, and the rest alkali A in the first step participates in the second step reaction. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 73% yield.
Example 4
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, pump B was fed with ethylsulfonyl chloride and the feed concentration and feed pump flow rate were adjusted so that 3-buten-1-ol: ethyl sulfonyl chloride: the molar ratio of triethylamine (base A) is 1:1.1:1.5, the reaction temperature of the first step is 50 ℃, and the reaction is carried out for 4 minutes. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 71% yield.
Example 5
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, pump D was fed with aqueous sodium hydroxide (base B) and 3-buten-1-ol was prepared by adjusting the feed concentration and feed pump flow rate: (S) -1-phenylethylamine: the molar ratio of sodium hydroxide is 1:1.0:1.0, the reaction temperature of the second step is 60 ℃, the reaction is carried out for 100 minutes, and the second micro-mixer is a Y-type mixer. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 66% yield.
Example 6
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in the embodiment, the pump C is fed with a mixed solution of (S) -1-phenethylamine and pyridine in acetonitrile, a pump D is not used, the material concentration and the flow rate of a feeding pump are regulated, the molar ratio of the (S) -1-phenethylamine to the pyridine is 1:1.5:3.0, and the reaction temperature in the second step is 260 ℃ for 10 minutes. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 64% yield.
Example 7
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, pump A was fed with 3-buten-1-ol and diisopropylethylamine (base A) in acetonitrile, pump D was fed with diisopropylethylamine in acetonitrile, and the feed concentration and feed pump flow rate were adjusted so that 3-buten-1-ol: (S) -1-phenylethylamine: the molar ratio of diisopropylethylamine (base B) was 1:1.2:2.0. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 76% yield.
Example 8
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, the feed concentration and feed pump flow rate were adjusted to give 3-buten-1-ol: the molar ratio of glyoxylic acid is 1:1.0, the reaction temperature after the intermediate II solution and the glyoxylic acid solution are mixed is 60 ℃, the reaction is carried out for 100 minutes, and the back pressure of a back pressure valve is 1.0Mpa. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 75% yield.
Example 9
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, the feed concentration and feed pump flow rate were adjusted to give 3-buten-1-ol: the molar ratio of glyoxylic acid is 1:3.0, the reaction temperature after the intermediate II solution and the glyoxylic acid solution are mixed is 160 ℃, the reaction is carried out for 10 minutes, and the back pressure of a back pressure valve is 3Mpa. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 69% yield.
Example 10
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, the feed of pump E was an N, N-dimethylacetamide solution of glyoxylate (pumped by pump E), and the material concentration and feed pump flow rate were adjusted so that the molar ratio of 3-buten-1-ol to glyoxylate was 1:1.8, the reaction temperature was 100℃and the reaction time was 60 minutes. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 73% yield.
Example 11
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, pump A was fed with 3-buten-1-ol, triethylamine in N, N-dimethylacetamide solution, and pump B was fed with methanesulfonic anhydride in N, N-dimethylacetamide solution. Pump E was fed glyoxylate (50% aqueous solution) with no solvent added. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 71% yield.
Example 12
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, pump A was fed with a mixture of 3-butene-1-ol and triethylamine (base A), no solvent was added, pump C was fed with a mixture of (S) -1-phenethylamine and diisopropylethylamine (base B), no solvent was added, and pump D was not used. Pump E was fed glyoxylate (50% aqueous solution) with no solvent added. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 75% yield.
Example 13
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
in this example, the pump A was fed with 3-butene-1-ol and triethylamine (base A) mixture without adding solvent, the material concentration and the feed pump flow rate were adjusted so that the molar ratio of 3-butene-1-ol, methylsulfonic anhydride and triethylamine (base A) was 1:1.1:3.0, the pump C was fed with (S) -1-phenethylamine, without adding solvent, without using pump D, without feeding base B, and the base A remaining in the first step was involved in the second reaction step. Pump E was fed glyoxylate (50% aqueous solution) with no solvent added. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 72% yield.
Example 14
The overall scheme of this embodiment is basically the same as that of embodiment 1, except that:
the reactor in this example is a microchannel reactor and the micromixer is a static mixer. The product obtained in this example was 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one in 77% yield.
Compared with the prior art, the invention provides a novel 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone synthesis process, the intermediate steps of the process do not need separation and purification, the total yield is stabilized at 64-77%, the complex operation flow is greatly simplified, the reaction time is greatly shortened, and the generation amount and variety of wastes are obviously reduced. Therefore, the synthesis process of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octane-7-ketone provided by the invention has the advantages of low cost, simple and convenient operation, high space-time efficiency, low emission of three wastes and the like.
Although embodiments of the present invention have been disclosed above, it is not limited to the details and embodiments shown and described, it is well suited to various fields of use for which the invention would be readily apparent to those skilled in the art, and accordingly, the invention is not limited to the specific details and illustrations shown and described herein, without departing from the general concepts defined in the claims and their equivalents.
Claims (7)
1. A process for the preparation of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one, characterized in that the 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one is synthesized by the steps of:
step (1), mixing the mixed solution of 3-butene-1-ol and alkali A and the activating reagent solution in a micromixer, and flowing into a first reactor for reaction to obtainThe intermediate I solution adopts acetonitrile as an organic solvent,N,NAt least one of dimethylacetamide, wherein the activating reagent is methylsulfonic anhydride, the reaction temperature is 0-60 ℃, and the residence time of the reaction mixture is 1-30 minutes;
step (2), the intermediate I solution is preparedS) Mixing 1-phenethylamine and alkali B solution in a micromixer, and flowing into a second reactor for reaction to obtain an intermediate II solution;
step (3), mixing the intermediate II solution with glyoxylic acid or glyoxylic acid aqueous polymer solution in a micromixer, and then flowing into a third reactor to react to obtain a target product 2- (. About.S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1]Octan-7-one; intermediate II solution: the mol ratio of glyoxylic acid or glyoxylic acid compound is 1 (1.0-3.0), the reaction temperature is 60-160 ℃, the reaction time is 10-100 minutes, and the back pressure of the back pressure valve is 1.0-3.0Mpa; the reactors in the steps (1) - (3) are microchannel reactors or serially connected coil reactors;
the chemical reaction process of the above synthetic method is as follows:
2. a process for the preparation of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one according to claim 1, wherein base a is one or more of triethylamine, pyridine, substituted pyridine, diisopropylethylamine, 1, 8-diazabicyclo [5.4.0] undec-7-ene.
3. A process for the preparation of 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one according to claim 2, wherein in step (1) 3-buten-1-ol: activating reagent: the molar ratio of the base A is 1.0: (1.0 to 1.5): (1.0 to 3.0).
4. The process for preparing 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one according to claim 3, wherein in step (2), the base B solution is one of a pure organic base, an organic solution of an organic base, or an aqueous solution of an inorganic base.
5. The process for preparing 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one according to claim 4, wherein the inorganic base is one or more of lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, lithium bicarbonate, potassium bicarbonate, sodium bicarbonate; the organic base is one or more of triethylamine, pyridine, 2, 6-lutidine, 4-dimethylaminopyridine, diisopropylethylamine and 1, 8-diazabicyclo [5.4.0] undec-7-ene.
6. 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] as claimed in claim 5]A process for the preparation of octan-7-one, characterized in that in step (2) the intermediate I solution: (S) -1-phenethylamine: the molar ratio of the alkali B is 1 (1.0-1.5): (0-3.0), the reaction temperature is 60-260 ℃ and the reaction time is 10-100 minutes.
7. The method of preparing 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one according to claim 6, wherein the micromixer in steps (1) - (3) is any one of a T-type micromixer, a Y-type micromixer, a multi-interactive thin-layer micromixer, a static micromixer, a chaotic micromixer, and a dynamic micromixer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210127004.0A CN114394976B (en) | 2022-02-11 | 2022-02-11 | 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210127004.0A CN114394976B (en) | 2022-02-11 | 2022-02-11 | 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114394976A CN114394976A (en) | 2022-04-26 |
| CN114394976B true CN114394976B (en) | 2023-05-02 |
Family
ID=81232072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210127004.0A Active CN114394976B (en) | 2022-02-11 | 2022-02-11 | 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114394976B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111548328A (en) * | 2020-05-18 | 2020-08-18 | 江苏阿尔法药业有限公司 | Method for preparing 2,3, 5-tribenzyloxy-D-ribonic acid-1, 4-lactone by oxidation in continuous flow microchannel reactor |
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007332105A (en) * | 2006-06-16 | 2007-12-27 | Osaka Univ | Method for chemical synthesis of pristane |
| FR2971783B1 (en) * | 2011-02-17 | 2013-02-15 | Rhodia Operations | PROCESS FOR HYDROXYLATION OF PHENOLS AND PHENOL ETHERS |
| CN111925514A (en) * | 2020-07-02 | 2020-11-13 | 西华大学 | Method for continuously producing high molecular weight polyether by adopting microchannel reactor |
-
2022
- 2022-02-11 CN CN202210127004.0A patent/CN114394976B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
| CN111548328A (en) * | 2020-05-18 | 2020-08-18 | 江苏阿尔法药业有限公司 | Method for preparing 2,3, 5-tribenzyloxy-D-ribonic acid-1, 4-lactone by oxidation in continuous flow microchannel reactor |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114394976A (en) | 2022-04-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114989112B (en) | Method for preparing enamine compound by utilizing photocatalysis micro-channel | |
| CN113264845B (en) | Method for continuously preparing chloramphenicol by using micro-reaction system | |
| CN111100088B (en) | Method for continuously synthesizing ethyl dithiahydroxamate | |
| CN114031602B (en) | Reaction process and device for continuously synthesizing 18-crown ether-6 | |
| CN109912520B (en) | 1, 5-benzodiazepine compound and preparation method thereof | |
| CN114394976B (en) | 2- ((S) -1-phenethyl) -6-oxa-2-azabicyclo [3.2.1] octan-7-one | |
| WO2023010649A1 (en) | Method for continuous synthesis of p-toluenesulfonyl chloride | |
| CN112574049A (en) | Novel method for preparing phenylglycine by using hydrocyanic acid | |
| CN116283952A (en) | Vitamin B 1 Is a fully continuous flow preparation method | |
| CN112921405B (en) | Method for synthesizing On-DNA pyrazolo [1,5-a ] pyrimidine compound | |
| CN113024446B (en) | Method for preparing amlodipine besylate intermediate by using micro-reaction device | |
| CN111574416B (en) | Method for preparing tiamulin from isothiourea salt and pleuromutilin p-toluenesulfonate | |
| CN105777669B (en) | The method that 2 ethyoxyl 5 (the base sulfonyl of 4 methyl piperazine 1) benzoic acid are prepared with gaultherolin | |
| CN110845504A (en) | Novel method for synthesizing pratinib | |
| CN111518148A (en) | Synthetic method of gastrodin intermediate | |
| CN114560865B (en) | Continuous flow synthesis method of (3 aS,6 aR) -lactone | |
| CN110283129A (en) | A method of synthesizing complete carbon-based substituted pyrimidines derivative | |
| CN110590775A (en) | Preparation method of intermediate of Abamebactam sodium of beta-lactamase inhibitor drug | |
| CN113248447B (en) | Method for preparing quinazolinone compound | |
| CN114940657B (en) | Amidine compound synthesized from N, N, N ', N' -tetramethyl ethylenediamine | |
| CN114805335B (en) | Continuous flow preparation method of statin side chain diol sulfone | |
| CN112921406B (en) | Method for synthesizing On-DNA 2-aminopyrimidine compound | |
| CN115043787B (en) | Preparation method of 2,4, 5-trisubstituted oxazole compound | |
| CN116813638A (en) | Method for preparing (+) -biotin by continuous flow debenzylation | |
| CN117050011B (en) | Method for synthesizing 2-methylquinoline by using vinyl acetate as raw material |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |