反应详情

温度

65 °C

A mixture of 5-chloromethyl-3-isopropyl-[1,2,4]oxadiazole (1.6 g, 10 mmol) and (RS)-3-hydroxypyrrolidine (960 mg, 11 mmol) were combined neat, diluted with MeCN (10 mL), and K2CO3 (2.75 g, 20 mmol) was added. The mixture was heated at 65° C. for 1 h, and was filtered upon cooling. The solvent was removed and the residue was taken up in CH2Cl2 and rinsed with water. The organic extract was dried over MgSO4, the solvent was removed, and the residue was taken up in ether and filtered in order to remove a small amount of quaternary ammonium byproduct. Solvent removal from the filtrate gave (RS)-3-hydroxy-1-[(3-isopropyl-1,2,4-oxadiazol-5-yl)methyl]pyrrolidine as an amber oil (1.72 g, 82% yield): 1H NMR (DMSO-d6) δ 4.76 (d, 1H, J=4.5 Hz), 4.19 (m, 1H), 3.90 (s, 2H), 3.05 (m, 1H), 2.79 (m, 1H), 2.69 (m, 1H), 2.53 (m, 1H), 2.43 (m, 1H), 1.98 (m, 1H), 1.54 (m, 1H), 1.25 (d, 6H, J=6.8 Hz); MS m/z 212.1 (M+).

1. additionwas added
2. filtrationwas filtered
3. temperatureupon cooling
4. customThe solvent was removed
5. washrinsed with water
6. extractionThe organic extract
7. dry with materialwas dried over MgSO4
8. customthe solvent was removed
9. filtrationfiltered in order
10. customto remove a small amount of quaternary ammonium byproduct
11. customSolvent removal from the filtrate