反応 #162321

反応方程式

(R)-1-(4-chloro-3-(1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-4-one

3-(t-butoxycarbonylamino)pyrrolidine

NaBH(OAc)3

→

t-butyl 1-(1-(4-chloro-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-4-yl)pyrrolidin-3-ylcarbamate

収率 50.0%

溶媒

dichloroethane

反応条件

後処理

1. 1
   その他The reaction mixture was quenched with aqueous saturated sodium bicarbonate
2. 2
   抽出extracted with dichloromethane
3. 3
   乾燥The organic layer was dried (Na2SO4)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The resulting crude was purified by flash chromatography (SiO2, 1-7% methanol in dichloromethane)

実験手順

To a stirred solution of (R)-1-(4-chloro-3-(1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-4-one (0.13 g, 0.32 mmol) and 3-(t-butoxycarbonylamino)pyrrolidine (0.24 g, 1.3 mmol) in dichloroethane (DCE) (2 mL) was added NaBH(OAc)3 (0.094 g, 0.44 mmol). The reaction mixture was heated at 80° C. for 4 h. The reaction mixture was quenched with aqueous saturated sodium bicarbonate and extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude was purified by flash chromatography (SiO2, 1-7% methanol in dichloromethane) to give t-butyl 1-(1-(4-chloro-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperidin-4-yl)pyrrolidin-3-ylcarbamate (0.092 g, 0.16 mmol, 31%).

出典