Reaktion #366071

Reaktionsgleichung

[2-(4-benzyloxy-phenyl)-1-(diethylamino-methyl)-ethyl]-carbamic acid tert-butyl ester

2,2,2-triflouroacetic acid

→

(S)-3-(4-benzyloxy-phenyl)-N1,N1-diethyl-propane-1,2-diamine

Ausbeute 90.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated at reduced pressure to a viscous amber oil to which
2. 2
   workup.ADDITIONwas added 30 mL saturated aqueous sodium bicarbonate solution
3. 3
   Extraktionthe resulting mixture extracted with three 20 mL portions of ethyl acetate
4. 4
   WaschenThe combined extracts were washed with two 50 mL portions of brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated at reduced pressure
7. 7
   Sonstigethe residue purified by column chromatography

Vorschrift

A solution of 171 mg (0.4 mmol) [2-(4-benzyloxy-phenyl)-1-(diethylamino-methyl)-ethyl]-carbamic acid tert-butyl ester in 2 mL dichloromethane was treated with 0.5 mL 2,2,2-triflouroacetic acid and the resulting solution stirred 3 hours at 25° C. The mixture was concentrated at reduced pressure to a viscous amber oil to which was added 30 mL saturated aqueous sodium bicarbonate solution and the resulting mixture extracted with three 20 mL portions of ethyl acetate. The combined extracts were washed with two 50 mL portions of brine, dried over anhydrous sodium sulfate, and concentrated at reduced pressure and the residue purified by column chromatography using ethyl acetate containing 1% methanol as eluent. There was obtained 112 mg (90%) of (S)-3-(4-benzyloxy-phenyl)-N1,N1-diethyl-propane-1,2-diamine as a clear, colorless oil.

Quelle