Reaktion #164189

Reaktionsgleichung

sodium triacetoxyborohydride

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

4-methylbenzaldehyde

AcOH

→

title compound

Ausbeute 54.9%

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

Ausbeute 54.9%

Lösungsmittel

cyclohexane

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle