Reaktion #81609

Reaktionsgleichung

ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate

trifluoracetic acid

→

title compound

Ausbeute 62.4%

Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]-benzenepropanoate

Ausbeute 62.4%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeevaporated
2. 2
   SonstigeThe residue was partitioned between ether and dilute sodium hydroxide solution
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with water
5. 5
   Trocknendried (MgSO4)
6. 6
   SonstigeThe solvent was evaporated
7. 7
   Sonstigethe residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide
8. 8
   workup.ADDITIONThe product containing fractions
9. 9
   Sonstigethe solvent evaporated

Vorschrift

A solution of ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate (2.36 g) and trifluoracetic acid (5 ml) in dichloromethane (25 ml) was allowed to stand at room temperature overnight and then evaporated. The residue was partitioned between ether and dilute sodium hydroxide solution. The organic layer was separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide. The product containing fractions were combined and the solvent evaporated to give the title compound as a gum (1.13 g), Rf 0.1 (SS 4). N.M.R. δ(CDCl3): 1.24 (3H,t), 1.48(2H,s), 2.61(2H,t), 2.73(2H,t), 2.90-2.98(4H,m), 3.93(2H,s), 4.14(2H,q), 6.88(2H,s), 6.91(1H,s), 6.96-7.03(2H,m), 7.12-7.18(2H,m).

Quelle