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

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.

1. concentrationThe mixture was concentrated at reduced pressure to a viscous amber oil to which
2. additionwas added 30 mL saturated aqueous sodium bicarbonate solution
3. extractionthe resulting mixture extracted with three 20 mL portions of ethyl acetate
4. washThe combined extracts were washed with two 50 mL portions of brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated at reduced pressure
7. customthe residue purified by column chromatography

ORD-Eintrag

ord-8aee0b5c5fdd4bf2873b509d1e7cc23f

Quelldatensatz

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06316440B1