反应详情

温度

75 °C

Place 1-cyclohexyl-4-hydroxymethyl-pyrrolidin-2-one (Preparation 2) (2.5 g, 12.7 mmol) and triphenylphosphene (3.7 g, 13.9 mmol) in a flask and add dry N,N-dimethyl-acetamide (20 mL). Add a solution of iodine (3.2 g, 12.7 mol) in N,N-dimethyl-acetamide (3 mL). Stir reaction for 24 hours. Quench the reaction with saturated sodium bisulfite (20 mL) and extract with methylene chloride. Dry over sodium sulfate, filter, and concentrate. Dissolve crude material in acetonitrile (100 mL) and add glacial acetic acid (15 mL) and zinc (12.4 g, 190.1 mmol), then heat to 75° C. and stir for 6 hours. Cool to room temperature, filter, and partition between water and methylene chloride. Separate layers and wash methylene chloride with saturated sodium bicarbonate. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (30-40% ethyl acetate in hexane) to yield 1.0 g (45%) of the title compound. NMR (CDCl3) δ 3.94 (m, 1H), 3.45 (m, 1H), 2.88 (dd, 1H), 2.55 (dd, 1H), 2.38 (m, 1H), 2.02 (dd, 1H), 1.78 (m, 2H), 1.68 (m, 3H), 1.35 (m, 4H), 1.09 (m, 4H).

1. customreaction for 24 hours
2. customQuench
3. customthe reaction with saturated sodium bisulfite (20 mL)
4. extractionextract with methylene chloride
5. dry with materialDry over sodium sulfate
6. filtrationfilter
7. concentrationconcentrate
8. dissolutionDissolve crude material in acetonitrile (100 mL)
9. stirringstir for 6 hours
10. temperatureCool to room temperature
11. filtrationfilter
12. custompartition between water and methylene chloride
13. washSeparate layers and wash methylene chloride with saturated sodium bicarbonate
14. dry with materialDry over sodium sulfate
15. filtrationfilter
16. concentrationconcentrate
17. customPurify by silica gel (30-40% ethyl acetate in hexane)