反应详情

To a solution of 1-(3-bromo-5-methoxymethoxy-phenyl)-3,3-dimethyl-pyrrolidine-2,5-dione (643 mg, 1.88 mmol) in dry THF (8 ml) (under nitrogen) was added a solution of borane-dimethylsulfide complex (1.7 ml, 16.9 mmol, 10.1M) via slow drop-wise addition. The material was stirred for 12 hours. The mixture was cooled (ice bath) and carefully quenched via the slow drop-wise addition of water (10 ml). Methylene chloride (60 ml), and water (50 ml) were added and the material shaken. The organic phase was collected and washed with brine (60 ml). The aqueous phases were back extracted with methylene chloride (2×50 ml). The organics were combined, dried (MgSO4), filtered and stripped to provide a crude oil. The material was adsorbed onto silica (12 g) and purified by silica gel chromatography, eluting with 5% to 9% ethyl acetate in hexanes to afford 517 mg of 1-(3-bromo-5-methoxymethoxy-phenyl)-3,3-dimethyl-pyrrolidine as a clear oil.

1. additionvia slow drop-wise addition
2. temperatureThe mixture was cooled (ice bath)
3. customcarefully quenched via the slow drop-wise addition of water (10 ml)
4. additionMethylene chloride (60 ml), and water (50 ml) were added
5. stirringthe material shaken
6. customThe organic phase was collected
7. washwashed with brine (60 ml)
8. extractionThe aqueous phases were back extracted with methylene chloride (2×50 ml)
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. customto provide a crude oil
12. custompurified by silica gel chromatography
13. washeluting with 5% to 9% ethyl acetate in hexanes