Reacción #52263

Ecuación de reacción

1,1′-(Azodicarbonyl)dipiperidine

methyl 3-(5-hydroxyindolyl)propanoate

3-(benzyloxycarbonylamino)propanol

tri-n-butylphosphine

→

title compound

Methyl 3-{5-[3-(benzyloxycarbonylamino)propoxy]indolyl}propanoate

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe reaction mixture was concentrated
2. 2
   Otrothe residue was purified by flash column chromatography on silica gel (0-2% ethyl acetate in methylene chloride)

Procedimiento

1,1′-(Azodicarbonyl)dipiperidine (370 mg, 1.5 mmol) was added to the solution of methyl 3-(5-hydroxyindolyl)propanoate (220 mg, 1.0 mmol), as prepared in step g of Example 5, 3-(benzyloxycarbonylamino)propanol (230 mg, 1.1 mmol) and tri-n-butylphosphine (305 mg, 1.5 mmol) in tetrahydrofuran (20 mL). After stirring at ambient temperature overnight, the reaction mixture was concentrated and the residue was purified by flash column chromatography on silica gel (0-2% ethyl acetate in methylene chloride) to give the title compound as an off white solid (310 mg, 76%). 1H-NMR (400 MHz, CDCl3) δ 7.35 (m, 5H), 7.22 (d, J=8.9 Hz, 1H), 7.09 (d, J=3.1 Hz, 1H), 7.07 (d, J=2.1 Hz, 1H), 6.86 (dd, J=8.8, 2.4 Hz, 1H), 6.38 (d, J=2.9 Hz, 1H), 5.11 (br s, 3H), 4.41 (t, J=6.8 Hz, 2H), 4.07 (t, J=5.9 Hz, 2H), 3.66 (s, 3H), 3.44 (q, J=6.3 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 2.02 (m, 2H).

Fuente