Reaktion #1093180

Reaktionsgleichung

acetic acid

2-Benzyloxy-5-bromobenzaldehyde

ethyl 4-aminomethylbenzoate

sodium borohydride

→

ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate

Lösungsmittel

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   workup.ADDITIONwas added
3. 3
   ExtraktionThe mixture was extracted with diethyl ether (4×100 ml)
4. 4
   Waschenthe extracts washed with saturated aqueous NaHCO3
5. 5
   Trocknendried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated

Vorschrift

2-Benzyloxy-5-bromobenzaldehyde and ethyl 4-aminomethylbenzoate were heated together at 100° C. for 1 hour. The mixture was cooled, dissolved in ethanol (100 ml) and sodium borohydride (1.3 g) was added. The mixture was stirred for 18 hours at ambient temperature, acidified with acetic acid and water (200 ml) was added. The mixture was extracted with diethyl ether (4×100 ml), the extracts washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and evaporated to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate which was purified by chromatography on silica gel eluting with CH2Cl2 then 5% ethyl acetate/CH2Cl2 (yield 11.4 g).

Quelle