As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO349,mainly used in chemical industry, its synthesis route is as follows.,141556-45-8
IMesHCl (0.503 g, 1.47 mmol) was loaded into an oven-dried 100 mL Schlenk flask and placed under a nitrogen atmosphere. Dry degassed THF (50mL) was added to the flask via cannula and a white slurry formed. The slurry was chilled to -78C in a dry ice/acetone bath and 1.OOmL of 1.6M nBuLi in hexane (1.6mmol) was added drop-wise. This reaction mixture was stirred for 30 minutes in the cold bath followed by 2 hours out of the bath to generate free carbene. The flask was then cooled a second time to -78C followed by addition of freshly distilled TMEDA (0.97 mL; 6.47 mmol) and 1.00 mL of 1.6 M nBuLi. The reaction mixture was stirred for 2 hours at -78C followed by addition of Mes2BF (0.473 g, 1.76 mmol). The reaction mixture was stirred for 3 hours while at -78C before warming to room temperature and stirring overnight. The resulting mixture was quenched with water and extracted with diethyl ether. An organic extract was dried over MgS04 followed by removal of volatiles in vaccuo. A resulting solid was dissolved in a minimum of diethyl ether and was precipitated by addition of hexane. The solid was collected by vacuum filtration and 0.723 g (89%) of the chelate product SMI was collected. X-ray quality crystals were grown using a saturated solution of THF layered with hexanes. 1H NMR (C6D6): delta = 1.67 (s, 3H, ArCH3), 1.68 (s, 3H, ArCH3), 1.85 (s, 3Eta, ArCH3), 2.04 (s, 3Eta, ArCH3), 2.07 (s, 3Eta, ArCH3), 2.08 (s, 3Eta, ArCH , 2.08 (s, 3Eta, ArCH3), 2.13 (s, 3Eta, ArCH3), 2.17 (s, 3Eta, ArCH3), 2.46 (s, 3Eta, ArCH3), 2.84 (d, 1Eta, 3JHH = 12.0 Hz, B-CH2), 2.88 (s, 3Eta, ArCH3), 3.06 (d, 1Eta, 3JHH = 12.0 Hz, B-CH2), 5.78 (d, 1H, 3JHH = 4.0 Hz, Imidazole-CH), 5.97 (s, 1H, ArH), 6.18 (s, 1Eta, ArH), 6.48 (s, 1Eta, ArH), 6.52 (s, 1Eta, ArH), 6.52 (s, 1Eta, ArH), 6.62 (d, 1 Eta, 3JHH = 4.0 Hz, Imidazole-CH), 6.72 (s, 1Eta, ArH), 6.73 (s, 1Eta, ArH), 6.73 (s, 1Eta, ArH). nB NMR (C6D6): delta = -1 1.2. 13C {} NMR (C6D6): delta = 19.1 (ArCH3), 19.1 (ArCH3), 20.0 (Ar H3), 20.8 (Ar H3), 20.8 (Ar H3), 21.0 (ArCH3), 21.0 (ArCH3), 24.0 (ArCH3), 24.9 (ArCH3), 27.7 (ArCH3), 27.9 (Ar H3), 33.5 (located by HSQC, B- H2), 120.0 (Imidazole-CH), 121.3 (Imidazole-CH), 125.3 (ArQ, 125.7 (ArQ, 6 ArCH located under the solvent signal via HSQC , 129.0 (ArCH), 130.3 (ArQ, 130.8 (ArCH), 131.5 (ArQ, 131.9 (ArQ, 133.0 (ArQ, 133.1 (ArQ, 134.4 (ArQ, 135.9 (ArQ, 137.0 (ArQ, 138.3 (ArQ, 138.7 (ArQ, 141.3 (ArQ, 141.9 (ArQ, 143.1 (ArQ, 145.4 (ArQ, 207.4 (N-C-N). Anal. Calcd. for C39H45N2B: C, 84.77; H, 8.21 ; N, 5.07.
With the synthetic route has been constantly updated, we look forward to future research findings about 1,3-Dimesityl-1H-imidazol-3-ium chloride,belong chiral-catalyst compound
Reference£º
Patent; LU, Jiasheng; WANG, Suning; KO, Soo-Bying; MCDONALD, Sean, Michael; YANG, Dengtao; WO2014/153648; (2014); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare