반응 #164189

반응 방정식

sodium triacetoxyborohydride

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

4-methylbenzaldehyde

AcOH

→

title compound

수율 54.9%

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

수율 54.9%

용매

cyclohexane

THF

반응 조건

후처리

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

실험 절차

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).

출처