Ortho-bicyclic amine compound and its preparation method and chiral product
A technology for cyclic amines and compounds, applied in the field of asymmetric synthesis, can solve the problems of cumbersome operation and narrow substrate application range.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
preparation example Construction
[0030] The present invention provides a method for preparing an o-bicyclic amine compound, the o-bicyclic amine compound is a compound of the structure shown in formula (4), the method comprising: in the presence of a chiral catalyst, the formula ( 1) The compound of the shown structure is subjected to an addition reaction with hydrogen, wherein the chiral catalyst is a complex of the structure shown in formula (2);
[0031] Formula (4)
[0032] Formula 1)
[0033] Wherein, X' is selected from CH or N; R 1 , R 2 , R 3 and R 4 each independently hydrogen, halogen, substituted or unsubstituted C 1 -C 10 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted arylbenzyl, wherein, for substituted alkyl, substituted cycloalkyl, substituted aryl and substituted arylbenzyl The substituents are each independently selected from one or more of fluorine, chlorine, bromine, nitro, methyl, methoxy, trifluorome...
preparation example 1
[0149] (1) Dissolve (R,R)-1,2-diphenyl-ethylenediamine (20mmol, purchased from Bailingwei Technology Co., Ltd. 24694 brand) in dichloromethane (30mL), and dissolve in P-methylphenylsulfonyl chloride (20mmol, purchased from Bailingwei Technology Co., Ltd. 283322 brand) in dichloroethane (30mL) was added dropwise (dropped within 30min), continued to react at 0°C for 1h, and then reduced pressure Rotary evaporation, the solid was separated and purified by column chromatography (the eluent was dichloromethane / methanol with a volume ratio of 10:1), so as to obtain 15 mmol of the formula (R, R)-(3-1-1-1) The chiral diamine shown has a yield of 75%, and the identification data of this chiral diamine is: 1 H NMR (300MHz, CDCl 3 ): δ7.31(d, J=8.3Hz, 2H), 7.18-7.09(m, 10H), 6.97(d, J=8.3Hz, 2H), 4.37(d, J=5.2Hz, 1H), 4.12 (d,J=5.2Hz,1H),2.32(s,3H),1.49(br,3H); 13 C NMR (75MHz, CDCl 3 ): δ142.5, 139.2, 137.2, 129.1, 128.4, 128.2, 127.5, 127.4, 127.0, 126.9, 126.6, 63.2, 60.5, 21.4. ...
preparation example 2
[0153] (1) According to the method of step (1) in Preparation Example 1, the difference is that methanesulfonyl chloride (20mmol, purchased from Alfa Aisha Chemical Co., Ltd. A13383 brand) is used instead of p-methylphenylsulfonyl chloride, and Reaction at 0°C for 1 h, thereby obtaining 14.6 mmol of chiral diamine represented by the formula (R,R)-(3-1-1-2), with a yield of 73%. The identification data of the chiral diamine for: 1 H NMR (300MHz, CDCl 3 ): δ7.34-7.26(m, 10H), 4.56(d, J=5.1Hz, 2H), 4.21(d, J=5.1Hz, 2H), 2.26(s, 3H); 13 C NMR (75MHz, CDCl 3 ): δ141.9, 139.7, 128.7, 128.6, 127.9, 127.8, 126.9, 126.7, 63.4, 60.2, 40.7.
[0154] (2) According to the method of step (2) in Preparation Example 1, the difference is that the chiral diamine used is the chiral diamine shown in the above formula (R, R)-(3-1-1-2) (145 mg, 0.5 mmol), recrystallized to obtain 275 mg of a red solid (ie, the complex shown in formula (R, R)-4j);
[0155] (3) According to the method of step (3...
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com