تفاعل #164189

معادلة التفاعل

sodium triacetoxyborohydride

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

4-methylbenzaldehyde

AcOH

→

title compound

المردود 54.9%

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

المردود 54.9%

المذيبات

cyclohexane

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر