Sodium Methoxide → HCID 18398756, compound

Participants

Reaction Conditions

Reaction Steps

1-tert-Butoxycarbonyl-2-bromo-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole (7.12 g) was added to a 1 mol solution of sodium methoxide in methanol (200 ml) and the resulting mixture warmed to 60° C. for 2 h. After cooling the solvent was removed under reduced pressure and the residue purified immediately by flash chromatography (SiO2; n-hexane/ethyl acetate 10:1) to give the product as a pale yellow oil (4.79 g); 1H (250 MHz, CDCl3) δ1.60-2.00 (6H, br m), 3.03 (2H, t, J=7.5 Hz), 3.42 (1H, m), 3.67 (1H, m), 3.78 (1H, m), 3.83 (1H, m), 4.63 (1H, t, J=2.5 Hz), 7.09 (2H, m), 7.25 (1H, d, J=5.0 Hz), 7.58 (1H, d, J=5.0 Hz) and 8.09 (1H, br s).

Provenance & Evidence