反应详情

A round-bottomed flask was charged with p-toluenesulfonyl chloride (16.01 g, 83.98 mmol, 1.5 equiv.) and 150 ml of anhydrous DCM. The solution was cooled to an ice-water bath and evacuated and purged with nitrogen. To this solution was added a solution of (3R)-(−)-N—BOC-3-hydroxypyrrolidine (purchased from Aldrich) (10.47 g, 55.99 mmol) in 50 mL of DCM, followed by DMAP (0.66 g) and triethylamine (16.2 mL). The solution was stirred under nitrogen overnight from 0° C. to rt. TLC (5% MeOH in DCM) showed the completion of the reaction. The reaction was quenched by addition of polymer-supported amine (8 g), stirred 30 min. 100 mL of DCM was added. The organic layer was washed with H3PO4 (1M, 2×50 mL), followed by NaHCO3 (50 mL), brine (50 mL), dried (K2CO3), filtered through a silica gel pad, and concentrated to obtain the title compound as a liquid, 15.82 g (82.8%).

1. temperatureThe solution was cooled to an ice-water bath
2. customevacuated
3. custompurged with nitrogen
4. customthe completion of the reaction
5. customThe reaction was quenched by addition of polymer-supported amine (8 g)
6. stirringstirred 30 min
7. addition100 mL of DCM was added
8. washThe organic layer was washed with H3PO4 (1M, 2×50 mL)
9. dry with materialdried (K2CO3)
10. filtrationfiltered through a silica gel pad
11. concentrationconcentrated