CN110330520A - A kind of synthetic method of methyl boron anhydride compound - Google Patents
A kind of synthetic method of methyl boron anhydride compound Download PDFInfo
- Publication number
- CN110330520A CN110330520A CN201910485814.1A CN201910485814A CN110330520A CN 110330520 A CN110330520 A CN 110330520A CN 201910485814 A CN201910485814 A CN 201910485814A CN 110330520 A CN110330520 A CN 110330520A
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- CN
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- Prior art keywords
- stainless steel
- steel cauldron
- anhydride compound
- synthetic method
- methyl
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- -1 methyl boron anhydride compound Chemical class 0.000 title claims abstract description 19
- 238000010189 synthetic method Methods 0.000 title claims abstract description 12
- 229910001220 stainless steel Inorganic materials 0.000 claims abstract description 30
- 239000010935 stainless steel Substances 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 10
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 claims abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 4
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 10
- 238000006073 displacement reaction Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 229910000831 Steel Inorganic materials 0.000 claims description 4
- 239000010959 steel Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- VMKAFJQFKBASMU-QGZVFWFLSA-N (r)-2-methyl-cbs-oxazaborolidine Chemical compound C([C@@H]12)CCN1B(C)OC2(C=1C=CC=CC=1)C1=CC=CC=C1 VMKAFJQFKBASMU-QGZVFWFLSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- JOYRNJIWPUZFBJ-IWTVZHICSA-N (2r)-3-[(1r)-2-[(1r,2r,5s,8as)-1,2,5-trimethyl-5-(4-methylpent-4-enyl)-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]-1-hydroxyethyl]-2-hydroxy-2h-furan-5-one Chemical compound C1([C@H](O)C[C@@]2(C)[C@H]3C([C@](CCC3)(C)CCCC(C)=C)=CC[C@H]2C)=CC(=O)O[C@H]1O JOYRNJIWPUZFBJ-IWTVZHICSA-N 0.000 description 1
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
- NVXLIZQNSVLKPO-UHFFFAOYSA-N Glucosereductone Chemical compound O=CC(O)C=O NVXLIZQNSVLKPO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229960000711 alprostadil Drugs 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QNDVLZJODHBUFM-WFXQOWMNSA-N okadaic acid Chemical compound C([C@H](O1)[C@H](C)/C=C/[C@H]2CC[C@@]3(CC[C@H]4O[C@@H](C([C@@H](O)[C@@H]4O3)=C)[C@@H](O)C[C@H](C)[C@@H]3[C@@H](CC[C@@]4(OCCCC4)O3)C)O2)C(C)=C[C@]21O[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]2O QNDVLZJODHBUFM-WFXQOWMNSA-N 0.000 description 1
- VEFJHAYOIAAXEU-UHFFFAOYSA-N okadaic acid Natural products CC(CC(O)C1OC2CCC3(CCC(O3)C=CC(C)C4CC(=CC5(OC(CC(C)(O)C(=O)O)CCC5O)O4)C)OC2C(O)C1C)C6OC7(CCCCO7)CCC6C VEFJHAYOIAAXEU-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/02—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in boilers or stills
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0053—Details of the reactor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/28—Moving reactors, e.g. rotary drums
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/05—Cyclic compounds having at least one ring containing boron but no carbon in the ring
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 kind of synthetic methods of methyl boron anhydride compound, it is reacted under certain pressure and temperature by sodium borohydride and boron trifluoride tetrahydrofuran and CO gas, then is refining to obtain the tetrahydrofuran solution of compounds methyl boric anhydride through distilling.Products therefrom obtains required chloromethyl ether compound by rectification under vacuum, and stable product quality effectively raises the adequacy of reaction by the setting on stainless steel cauldron.
Description
Technical field
The present invention relates to a kind of synthetic methods of methyl boron anhydride compound.
Background technique
(R) -2- methyl-CBS- oxazaborolidine is one kind of CBS class catalyst.Such catalyst can be in borine tetrahydro furan
Prochiral ketones are reduced into corresponding chiral, secondary alcohols with highly-solid selectively under the effect of muttering.It can be with highly-solid selectively, high yield
Reductone, be widely used in the asymmetric reduction reaction of prochiral ketones, apply also for chiral synthesis 'alpha '-hydroxy acids, alpha-amido
Acid, the symmetrical ferrocene glycol of C2, propargyl alcohol.In addition, in prostaglandin E1, dysidiolide, okadaic acid are fully synthetic
The reduction reaction of (R) -2- methyl-CBS- oxazaborolidine catalysis is used；A kind of current synthesis side of methyl boron anhydride compound
Method, design is unreasonable, and stable product quality is poor and inconvenient for operation.
Summary of the invention
The object of the present invention is to provide a kind of synthetic methods of methyl boron anhydride compound, the advantage is that, use
Hydrogen chloride gas is passed through under cryogenic in the aaerosol solution of alcohol and paraformaldehyde, products therefrom is obtained by rectification under vacuum
Required chloromethyl ether compound, stable product quality, gas phase purity > 95%, and also it is used during synthesis
Equipment can be such that it more fully reacts.
Above-mentioned technical purpose of the invention has the technical scheme that a kind of methyl boron anhydride compound
Synthetic method, comprising the following steps:
(1) 28.4 grams of sodium borohydride are weighed first to be placed in the stainless steel cauldron with constant pressure addition tank, are added 1.0kg's
Anhydrous tetrahydro furan, nitrogen displacement, separately weighs 223.6 grams of boron trifluoride tetrahydrofuran solution of 50% and is placed in constant pressure addition tank
For use；
(2) carbon monoxide displacement nitrogen is filled in reaction kettle by steel cylinder, pressure is 2 ~ 4atm, stirs one time on one side and is added dropwise three
Boron fluoride tetrahydrofuran, temperature control 25 DEG C ~ 30 DEG C, continue to be stirred to react after dripping off；
(3) with nitrogen displacement carbon monoxide, 5g acetone is added in liquid, and stirring starts rectifying after five minutes, collects evaporating for 78-81 degree
Get methyl boron anhydride compound
The present invention is further arranged to: keeping pressure in 2 ~ 4atm during step (2) stirring.；Reaction 8 ~ 12 hours.
The present invention is further arranged to: the stainless steel cauldron with constant pressure addition tank includes that stainless steel cauldron and setting exist
Constant pressure addition tank on the stainless steel cauldron, the stainless steel cauldron are located on security platform, wherein described stainless
Steel reaction kettle is equipped with agitating device, feed inlet and nitrogen inlet, and the two sides of the security platform are equipped with lift supporting rod, institute
The upper and lower ends for stating lift supporting rod are equipped with driving wheel, and wherein clockwise and anticlockwise motor and driving wheel are rotatablely connected；Two driving wheels
Between be equipped with movable chain, the two sides of the stainless steel cauldron are equipped with casing, and wherein the upper and lower ends of described sleeve pipe are all provided with
There is telescopic rod, the other end of each telescopic rod is connected and fixed with rail rods；One end of connecting rod connect solid with movable chain
The fixed and other end is fixed with casing connection；Cylinder is fixed on lift supporting rod and cylinder axis is connected and fixed with the connecting rod.
The present invention is further arranged to: wherein the connecting rod is equipped with the sliding sleeve being slidably connected with rail rods.
The present invention is further arranged to: the security platform is equipped with gag lever post, and the gag lever post is equipped with sliding in institute
The idler wheel for stating stainless steel cauldron surface can use idler wheel auxiliary when stainless steel cauldron moves up and down, guarantee movement
Stationarity.
During agitating device work, clockwise and anticlockwise motor is moved by driving wheel drive activity chain, in this way
The connecting rod connecting with movable chain drives stainless steel cauldron to move up and down by casing, in order to guarantee the stationarity of movement,
And then the trajectory synchronization cylinder operation of driving wheel movement, slides in rail rods in this way and is slided, further improved stainless
The stationarity and agitating device cooperation of steel reaction kettle movement, react the material of the inside sufficiently；When casing rises to telescopic rod
When top, clockwise and anticlockwise motor overturning is declined, and when dropping to the bottom of telescopic rod, then is risen, and is moved back and forth in this way.
In conclusion the invention has the following advantages:
1, using in the aaerosol solution that hydrogen chloride gas is passed through to alcohol and paraformaldehyde under cryogenic, products therefrom is passed through
It crosses rectification under vacuum and obtains required chloromethyl ether compound, stable product quality, gas phase purity > 95%.
2, the adequacy of reaction is effectively raised by the setting on stainless steel cauldron.
Detailed description of the invention
Fig. 1 is overall schematic.
Specific embodiment
Below in conjunction with attached drawing, invention is further described in detail.
A kind of embodiment: synthetic method of methyl boron anhydride compound, comprising the following steps:
(1) 28.4 grams of sodium borohydride (0.75mol) are weighed first to be placed in the stainless steel cauldron with constant pressure addition tank, are added
Enter the anhydrous tetrahydro furan of 1.0kg, nitrogen displacement separately weighs 223.6 gram (1.0 of boron trifluoride tetrahydrofuran solution of 50%
Mol it) is placed in constant pressure addition tank stand-by；
(2) carbon monoxide displacement nitrogen is filled in reaction kettle by steel cylinder, pressure is 2 ~ 4atm, stirs one time on one side and is added dropwise three
Boron fluoride tetrahydrofuran, temperature control 25 DEG C ~ 30 DEG C, continue to be stirred to react after dripping off；Kept during stirring pressure 2 ~
4atm.；Reaction 8 ~ 12 hours.
(3) with nitrogen displacement carbon monoxide, 5g acetone is added in liquid, and stirring starts rectifying after five minutes, collects 78-81 degree
Fraction obtain methyl boron anhydride compound, yield 85%.
The stainless steel cauldron with constant pressure addition tank includes stainless steel cauldron 1 and is arranged in the stainless steel reaction
Constant pressure addition tank 2 on kettle 1, the stainless steel cauldron 1 are located on security platform 3, and the security platform 3 is equipped with limit
Bar 16, the gag lever post 16 are equipped with sliding in the idler wheel 16-1 on 1 surface of stainless steel cauldron.
Wherein the stainless steel cauldron 1 is equipped with agitating device 4, feed inlet 5 and nitrogen inlet 6, the security platform 3
Two sides be equipped with lift supporting rod 7, the upper and lower ends of the lift supporting rod 7 are equipped with driving wheel 8, wherein clockwise and anticlockwise motor
17 are rotatablely connected with driving wheel 8；Movable chain 9 is equipped between two driving wheels 8, the two sides of the stainless steel cauldron 1 are all provided with
There is casing 10, wherein the upper and lower ends of described sleeve pipe 10 are equipped with telescopic rod 11, the other end and rail of each telescopic rod 11
Road bar 12 is connected and fixed；One end of connecting rod 13 is connected and fixed with movable chain 9 and the other end is connected and fixed with casing 10；Cylinder
14 are fixed on lift supporting rod 7 and cylinder axis is connected and fixed with the connecting rod 13.
Wherein the connecting rod 13 is equipped with the sliding sleeve 15 being slidably connected with rail rods 12.
During agitating device 4 works, clockwise and anticlockwise motor 17 is moved by 8 drive activity chain 9 of driving wheel,
The connecting rod 13 connecting in this way with movable chain 9 drives stainless steel cauldron 1 to move up and down by casing 10, in order to guarantee to move
Stationarity, the trajectory synchronization cylinder 14 that and then driving wheel 8 moves works, and such sliding sleeve 15 slided in rail rods 12,
It is further to improve the stationarity and the cooperation of agitating device 4 that stainless steel cauldron 1 moves, react the material of the inside sufficiently；When
When casing rises to the top of telescopic rod, clockwise and anticlockwise motor overturning is declined, when dropping to the bottom of telescopic rod, then on
It rises, moves back and forth in this way.
This specific embodiment is only explanation of the invention, is not limitation of the present invention, those skilled in the art
Member can according to need the modification that not creative contribution is made to the present embodiment after reading this specification, but as long as at this
All by the protection of Patent Law in the scope of the claims of invention.
Claims (5)
1. a kind of synthetic method of methyl boron anhydride compound, it is characterised in that: the following steps are included:
(1) 28.4 grams of sodium borohydride are weighed first to be placed in the stainless steel cauldron with constant pressure addition tank, are added 1.0kg's
Anhydrous tetrahydro furan, nitrogen displacement, separately weighs 223.6 grams of boron trifluoride tetrahydrofuran solution of 50% and is placed in constant pressure addition tank
For use；
(2) carbon monoxide displacement nitrogen is filled in reaction kettle by steel cylinder, pressure is 2 ~ 4atm, stirs one time on one side and is added dropwise three
Boron fluoride tetrahydrofuran, temperature control 25 DEG C ~ 30 DEG C, continue to be stirred to react after dripping off；
(3) with nitrogen displacement carbon monoxide, 5g acetone is added in liquid, and stirring starts rectifying after five minutes, collects evaporating for 78-81 degree
Get methyl boron anhydride compound.
2. a kind of synthetic method of methyl boron anhydride compound according to claim 1, it is characterised in that: the step
(2) keep pressure in 2 ~ 4atm during stirring;Reaction 8 ~ 12 hours.
3. a kind of synthetic method of methyl boron anhydride compound according to claim 1, it is characterised in that: band constant pressure addition
The stainless steel cauldron of tank includes the constant pressure addition tank of stainless steel cauldron (1) and setting on the stainless steel cauldron (1)
(2), the stainless steel cauldron (1) is located on security platform (3), wherein the stainless steel cauldron (1) is equipped with stirring
The two sides of device (4), feed inlet (5) and nitrogen inlet (6), the security platform (3) are equipped with lift supporting rod (7), described
The upper and lower ends of lift supporting rod (7) are equipped with driving wheel (8), and wherein clockwise and anticlockwise motor (17) and driving wheel (8) are rotatablely connected；
Movable chain (9) is equipped between two driving wheels (8), the two sides of the stainless steel cauldron (1) are equipped with casing (10), wherein
The upper and lower ends of described sleeve pipe (10) are equipped with telescopic rod (11), the other end of each telescopic rod (11) and rail rods (12)
It is connected and fixed；One end of connecting rod (13) is connected and fixed with movable chain (9) and the other end is connected and fixed with casing (10)；Cylinder
(14) it is fixed on lift supporting rod (7) and cylinder axis is connected and fixed with the connecting rod (13).
4. a kind of synthetic method of methyl boron anhydride compound according to claim 3, it is characterised in that: the wherein company
Extension bar (13) is equipped with the sliding sleeve (15) being slidably connected with rail rods (12).
5. a kind of synthetic method of methyl boron anhydride compound according to claim 3, it is characterised in that: the safety is flat
Platform (3) is equipped with gag lever post (16), and the gag lever post (16) is equipped with sliding in the idler wheel on the stainless steel cauldron (1) surface
(16-1).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910485814.1A CN110330520A (en) | 2019-06-05 | 2019-06-05 | A kind of synthetic method of methyl boron anhydride compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910485814.1A CN110330520A (en) | 2019-06-05 | 2019-06-05 | A kind of synthetic method of methyl boron anhydride compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110330520A true CN110330520A (en) | 2019-10-15 |
Family
ID=68140329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910485814.1A Pending CN110330520A (en) | 2019-06-05 | 2019-06-05 | A kind of synthetic method of methyl boron anhydride compound |
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| Country | Link |
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| CN (1) | CN110330520A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101274938A (en) * | 2007-03-27 | 2008-10-01 | 上海威智医药科技有限公司 | Preparation for (S) or (R)-2-methyl-CBS-chiral oxazaborolidine and toluene solution thereof |
| CN104163825A (en) * | 2013-05-20 | 2014-11-26 | 重庆圣华曦药业股份有限公司 | Improved methylboronic acid preparation method |
| US20160264514A1 (en) * | 2013-10-15 | 2016-09-15 | Toa Eiyo Ltd. | 4-aminomethylbenzoic acid derivative |
-
2019
- 2019-06-05 CN CN201910485814.1A patent/CN110330520A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101274938A (en) * | 2007-03-27 | 2008-10-01 | 上海威智医药科技有限公司 | Preparation for (S) or (R)-2-methyl-CBS-chiral oxazaborolidine and toluene solution thereof |
| CN104163825A (en) * | 2013-05-20 | 2014-11-26 | 重庆圣华曦药业股份有限公司 | Improved methylboronic acid preparation method |
| US20160264514A1 (en) * | 2013-10-15 | 2016-09-15 | Toa Eiyo Ltd. | 4-aminomethylbenzoic acid derivative |
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Application publication date: 20191015 |
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