Unlock instant, AI-driven research and patent intelligence for your innovation.
Method for preparation of tetrahydropyrrole
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A tetrahydropyrrole and chiral technology, applied in the field of heterocyclic compound chemistry, can solve problems such as unsatisfactory product selectivity, and achieve the effects of mild conditions, simple operation and easy availability of raw materials
Inactive Publication Date: 2013-11-13
WUHAN UNIV
View PDF15 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
However, these methods often require high temperature and high pressure and special catalysts, and the product selectivity is often not ideal
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 1
[0022] (2R, 3R)-1,1,4,4-tetraphenylbutanetetraol 4.26g (10mmol) and tributyl borate 1.2g (5mmol) were mixed in toluene and refluxed for several hours, the toluene solution was concentrated, and hand Spiroboronic acid white solid, more than 90% yield; m.p.403-405℃; [α] D 20 =+167.3 (c 0.22, DMSO); IR (KBr, cm -1 ): 3436, 3058, 2916, 1598, 1492, 1447, 1063, 698; 1 H-NMR (DMSO-d 6 , 300MHz): δ7.06-6.96(m, 32H, Ar-H), 6.78-6.68(m, 8H, Ar-H), 4.47(s, 4H, C-H); 4.20(s, br.4H,- OH); 13 C-NMR (CDCl 3 , 75MHz): δ 149.1, 147.0, 145.1, 128.4, 127.9, 127.5, 126.6, 126.1, 81.1, 78.8. 56 h 49 BO 8 -H Calculated value: 859.3422.
[0023] Get the above-prepared chiral spiroboronic acid 0.88g (1mmol) and (S)-proline 0.12g (1mmol) to reflux overnight in toluene, then cool to give (S)-proline decarboxylation product tetrahydropyrrole The white precipitate of the chiral spiroborate, the yield is higher than 90%, m.p.>300°C; 1 H NMR (DMSO-d 6 , 300MHz): δ8.48(s, 2H, N-H, plus D 2 O), ...
Embodiment 2
[0027] The chiral spiroboronic acid and (S)-proline prepared in Example 1 were mixed equimolarly in benzene and refluxed for several hours, then cooled to give the chiral spiroboronic acid of (S)-proline decarboxylation product tetrahydropyrrole. White precipitate of borate. Treatment as in Example 1 gave the tetrahydropyrrole.
Embodiment 3
[0029] The chiral spiroboronic acid and (S)-proline prepared in Example 1 were mixed equimolarly in acetonitrile and refluxed for several hours, then cooled to give the chiral spiroboronic acid of (S)-proline decarboxylation product tetrahydropyrrole. White precipitate of borate. Treatment as in Example 1 gave the tetrahydropyrrole.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
Abstract
The invention relates to a method for preparation of tetrahydropyrrole, which is a five-membered nitrogen heterocyclic compound and an important block in synthesis of alkaloid and drugs. The method is characterized in that the tetrahydropyrrole is prepared via decarboxylation of natural (S)-proline in the presence of spiro borate similar to boron neomycin. The preparation method has significant advantages that raw materials can be obtained easily, no metal compound catalyst or expensive oxidant is added, the operation is carried out under the atmospheric pressure, the reaction selectivity is good, no toxic products or byproducts can be produced, the raw materials can be recycled, and the yield of tetrahydropyrrole is high.
Description
technical field [0001] The invention relates to a new preparation method of tetrahydropyrrole, a saturated five-member nitrogen heterocyclic compound, and belongs to the field of heterocyclic compound chemistry. Background technique [0002] Tetrahydropyrrole (pyrrolidine), is a variety of alkaloids and chemotherapeutic agents containing pyrrolidine, such as: Buglomedil (Bulglomedil, for the treatment of cerebrovascular diseases, etc.), bepridil (Bepridil, for angina pectoris) Cardiovascular disease treatment), Acrivastine (Acrivastine, antisensitivity agent, used for the treatment of rhinitis, etc.), pyrrolidine oligomer analgesic (Riggs-Sauthier, J.PCT Int.Appl.2010, WO 2010132693) , iminosaccharide enzymes [inhibitors of glycosylase, glycosyltransferase, α-L-fucosidase (fucosidase), etc., have important application prospects in the treatment of viral infections, cancer and reproductive disorders, etc.], etc. It is an important building block, and its derivatives are of g...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More