反応 #164189

反応方程式

sodium triacetoxyborohydride

amino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

4-methylbenzaldehyde

AcOH

→

title compound

収率 54.9%

(4-methyl-benzylamino)-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

収率 54.9%

溶媒

cyclohexane

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction is stirred at RT for 1.5 hours
2. 2
   その他the mixture is evaporated to dryness
3. 3
   その他The crude is purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5)

実験手順

To a solution of amino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (I76) (100 mg, 0.38 mmol) in dry THF (3.84 mL), are added 4-methylbenzaldehyde (68 mL, 0.57 mmol) and AcOH (0.5 mL, 8.73 mmol). The mixture is stirred at RT and sodium triacetoxyborohydride (163 mg, 0.77 mmol) is added. The reaction is stirred at RT for 1.5 hours then cyclohexane is added and the mixture is evaporated to dryness. The crude is purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5) to obtain the title compound as a colorless oil (76 mg, 54% yield, mixture of diastereoisomers).

出典