The chiral-catalyst compound, cas is 22795-99-9 name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine, mainly used in chemical industry, its synthesis route is as follows.,22795-99-9
Example 24 (S)-(-)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-3,6-dibenzyloxy-2-methoxybenzamide (Method A) A solution of 3,6-dibenzyloxy-2-methoxybenzamide acid (120 mg, 0.33 mmol), thionyl chloride (120 mg, 1 mmol) and two drops of dimethylformamide as catalyst in 5 ml toluene was stirred at 60¡ã C. for 1.5 h. The solvent was evaporated and the residue dissolved in CH2 Cl2 and evaporated again. This residue was dissolved in 8 ml CH2 Cl2 and a solution of (S)-(-)-1-ethyl-2-aminomethylpyrrolidine (65 mg, 0.5 mmol) in 2 ml CH2 Cl2 was added. After stirring overnight at room temperature the solvent was evaporated and the residue partitioned between 2M HCl and ether. The aqueous phase was made alkaline, extracted with CH2 Cl2, dried (Na2 SO4) and evaporated to give a crude product. Purification by chromatography on SiO2 with iPr2 O/hexane/MeOH/NH3 69:20:10:1 as eluent gave 145 mg (93percent) pure title compound. M.p. 121¡ã-123¡ã C. [alpha ]D22 =-42¡ã (c=2.8, acetone). 1 H NMR (CDCl3)delta7.39 and 7.38)two s, CH2 Ph), 6.89 and 6.59 (AB, 4-H and 5-H), 5.06 and 5.03 (two s, CH2 Ph), 3.95 (s, OMe) ppm. Mass spectrum (EI, 70 eV): m/z 474 (M, 0.13percent), 347 (ArCO, 0.33percent), 98 (100percent), 91 (12percent)
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Reference£º
Patent; Astra Lakemedel Akteibolag; US5240957; (1993); A;,
Chiral Catalysts
Chiral catalysts – SlideShare