Reaktion #822893

Reaktionsgleichung

NaHCO3

glycine benzyl ester hydrochloride

4-bromobenzaldehyde

acetic acid

Sodium triacetoxyborohydride

→

80A

Ausbeute 64.0%

benzyl 2-(4-bromobenzylamino)acetate

Ausbeute 64.0%

Lösungsmittel

DCE

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a clear solution
2. 2
   Extraktionextracted with CH2Cl2 (3×)
3. 3
   ExtraktionThe combined organic extract
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude product was purified via flash chromatography (0 to 100% EtOAc in hexanes)

Vorschrift

To a suspension of glycine benzyl ester hydrochloride (2.02 g, 10.0 mmol) and 4-bromobenzaldehyde (1.85 g, 10.0 mmol) in 50 mL DCE, was added acetic acid (2.9 mL, 50 mmol) and TEA (1.4 mL, 10.0 mmol) to give a clear solution. Sodium triacetoxyborohydride (4.24 g, 20.0 mmol) was added. The suspension was stirred at rt for 17 h. The mixture was neutralized with sat. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extract washed with brine, dried (Na2SO4) and concentrated. The crude product was purified via flash chromatography (0 to 100% EtOAc in hexanes) to afford 80A (2.13 g, 64%). MS (ESI) m/z 334.0 (M+H)+.

Quelle