Reaktion #168143

Reaktionsgleichung

(S)-1-(4-Bromo-phenyl)-ethylamine

acetic acid

3-hydroxy-4-methoxy-3-phenyl-butyraldehyde

→

title compound

4-[(S)-1-(4-Bromo-phenyl)-ethylamino]-1-methoxy-2-phenyl-butan-2-ol

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooling bath was removed
2. 2
   workup.ADDITIONThen, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added
3. 3
   workup.STIRRINGthe resulting mixture was stirred for another 30 min
4. 4
   ExtraktionThe mixture was extracted with ethyl acetate
5. 5
   Waschenthe combined extracts were washed with water and brine
6. 6
   TrocknenAfter drying (MgSO4)
7. 7
   Sonstigethe solvent was removed

Vorschrift

(S)-1-(4-Bromo-phenyl)-ethylamine (0.93 g), NaHB(O2CH3)3 (0.98 g), and acetic acid (0.27 mL) were added in the given order to a solution of 3-hydroxy-4-methoxy-3-phenyl-butyraldehyde (0.90 g) in tetrahydrofuran (20 mL) at ca. 10-15° C. The cooling bath was removed and the mixture was stirred at room temperature for 2 h. Then, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added and the resulting mixture was stirred for another 30 min. The mixture was extracted with ethyl acetate and the combined extracts were washed with water and brine. After drying (MgSO4), the solvent was removed to give the title compound which was used without further purification.

Quelle