反应详情

PS-carbodiimide (1.39 mmol/g) resin beads (2.1 g, 3 mmol) are added to a 10 mL CHCl3/BuOH/MeCN (5:1:1) mixture of nicotinic acid (278 mg, 2 mmol), (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (231 mg, 1.5 mmol), HOBt (300 mg, 2.2 mmol), and triethylamine (0.30 mL, 2.2 mmol). The mixture is shaken at room temperature for 3 days. The reaction mixture is filtered and the beads are washed alternately with MeOH, then CH2Cl2, and the filtrate is concentrated in vacuo. The crude material product is partially purified by a SCX column (MeOH wash, elution with 2M NH3 in MeOH. Further purification is accomplished using silica-gel column chromatography (gradient: 100% CH2Cl2 to 10% 2M NH3 in MeOH/CH2Cl2) to give the title compound (200 mg, 73%). MS (ES+) 276.1 (M+H)+.

1. filtrationThe reaction mixture is filtered
2. washthe beads are washed alternately with MeOH
3. concentrationCH2Cl2, and the filtrate is concentrated in vacuo
4. customThe crude material product is partially purified by a SCX column (MeOH
5. washwash
6. washelution with 2M NH3 in MeOH
7. customFurther purification