反応 #41034

反応方程式

3-(5-trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionaldehyde

(1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane

AcOH

NaBH(AcO)3

DCE

DCE

→

title compound

収率 51.0%

5-(trifluoromethyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

収率 51.0%

溶媒

Ethyl acetate

反応条件

後処理

1. 1
   洗浄the solution washed with aqueous saturated NaHCO3
2. 2
   乾燥The organic phase was dried (Na2SO4)
3. 3
   その他evaporated
4. 4
   その他The crude was purified by flash chromatography with DCM-MeOH—NH4OH (97-3-1)

実験手順

To a solution of 3-(5-trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionaldehyde (Prep21, 0.05 g, 0.21 mmol) in DCE (1 mL), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 0.08 g, 0.35 mmol) in DCE (1 mL), AcOH (20 μl, 0.36 mmol) and NaBH(AcO)3 (0.09 g, 0.42) were added and the mixture was stirred at room temperature overnight. Ethyl acetate was added and the solution washed with aqueous saturated NaHCO3. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (97-3-1) to give the title compound (0.04 mg, 51% yield) as a free base.

出典