ethyl 4-[di(propan-2-yl)amino]-2-phenylbutanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-Diisopropyl-3-carbamyl-3-phenylpropanamine (26.5 g 0.100 mol) was added into aqueous ethanol (90%, 300 mL) containing conc. HNO3 (13.3 g, 0.21 mol) and refluxed for five days. Most of the solvent was evaporated under reduced pressure and the residue was mixed with water/diethyl ether. The organic phase was washed once with water. The combined aqueous phases were made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were then dried (Na2SO4) and the solvent evaporated. The crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3), to afford the title compound as a colourless liquid, 20.1 g (68.7%): 1H NMR (CDCl3) δ0.96 (m, 12H), 1.21 (t, 3H), 1.81 (m, 1H), 2.22 (m, 1H), 2.40 (t, 2H), 3.66 (dd, 1H), 4.12 (m, 2H), 7.20-7.32 (m, 5H). refluxed for five days Most of the solvent was evaporated under reduced pressure the residue was mixed with water/diethyl ether The organic phase was washed once with water extracted twice with diethyl ether The combined organic phases were then dried (Na2SO4) the solvent evaporated The crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-Diisopropyl-3-carbamyl-3-phenylpropanamine (26.5 g 0.100 mol) was added into aqueous ethanol (90%, 300 mL) containing conc. HNO3 (13.3 g, 0.21 mol) and refluxed for five days. Most of the solvent was evaporated under reduced pressure and the residue was mixed with water/diethyl ether. The organic phase was washed once with water. The combined aqueous phases were made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were then dried (Na2SO4) and the solvent evaporated. The crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3), to afford the title compound as a colourless liquid, 20.1 g (68.7%): 1H NMR (CDCl3) δ0.96 (m, 12H), 1.21 (t, 3H), 1.81 (m, 1H), 2.22 (m, 1H), 2.40 (t, 2H), 3.66 (dd, 1H), 4.12 (m, 2H), 7.20-7.32 (m, 5H). refluxed for five days Most of the solvent was evaporated under reduced pressure the residue was mixed with water/diethyl ether The organic phase was washed once with water extracted twice with diethyl ether The combined organic phases were then dried (Na2SO4) the solvent evaporated The crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N-Diisopropyl-3-carbamyl-3-phenylpropanamine (26.5 g 0.100 mol) was added into aqueous ethanol (90%, 300 mL) containing conc. HNO3 (13.3 g, 0.21 mol) and refluxed for five days. Most of the solvent was evaporated under reduced pressure and the residue was mixed with water/diethyl ether. The organic phase was washed once with water. The combined aqueous phases were made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were then dried (Na2SO4) and the solvent evaporated. The crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3), to afford the title compound as a colourless liquid, 20.1 g (68.7%): 1H NMR (CDCl3) δ0.96 (m, 12H), 1.21 (t, 3H), 1.81 (m, 1H), 2.22 (m, 1H), 2.40 (t, 2H), 3.66 (dd, 1H), 4.12 (m, 2H), 7.20-7.32 (m, 5H). refluxed for five days Most of the solvent was evaporated under reduced pressure the residue was mixed with water/diethyl ether The organic phase was washed once with water extracted twice with diethyl ether The combined organic phases were then dried (Na2SO4) the solvent evaporated The crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3)