Réaction #52263

Équation de réaction

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

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source