Réaction #164189

Équation de réaction

sodium triacetoxyborohydride

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

4-methylbenzaldehyde

AcOH

→

title compound

Rendement 54.9%

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

Rendement 54.9%

Solvants

cyclohexane

THF

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source