反应详情

To a stirred solution of tert-butyl 3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)carbonyl]pyrrolidine-1-carboxylate (3.39 g, 7.19 mmol) in THF (60 ml) was added a 1M solution of borane in THF (21.6 ml, 21.6 mmol) and the reaction heated to reflux for 4 hours. The cooled reaction mixture was then cautiously quenched by addition of methanol then solvents removed in vacuo to give a white solid. To this was then added saturated HCl in methanol (150 ml) and heated to reflux for 1 hour. The reaction mixture was then evaporated to dryness, partitioned between 2M NaOH and DCM, extracted twice, combined organics dried (Na2SO4), filtered and evaporated to a colorless oil. This was then purified on Isco™ Companion (40 g column: 20% methanolic ammonia/DCM) to give the product N-(3,4-dichlorophenyl)-4-(pyrrolidin-3-ylmethyl)piperazine-1-carboxamide as a white foam (444 mg, 1.24 mmol, 17%).

1. temperaturethe reaction heated
2. temperatureto reflux for 4 hours
3. customThe cooled reaction mixture
4. customwas then cautiously quenched by addition of methanol
5. customsolvents removed in vacuo
6. customto give a white solid
7. temperatureto reflux for 1 hour
8. customThe reaction mixture was then evaporated to dryness
9. custompartitioned between 2M NaOH and DCM
10. extractionextracted twice
11. dry with materialcombined organics dried (Na2SO4)
12. filtrationfiltered
13. customevaporated to a colorless oil
14. customThis was then purified on Isco™ Companion (40 g column: 20% methanolic ammonia/DCM)