p-Toluenesulfonic acid → HCID 23513934, compound

Participants

Reaction Steps

2-[4-[(allyloxy)methyl]-1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamide (239 mg) is dissolved in MeOH/H2O=9/1 (10 ml) then 10% Pd/C (12 mg) and p-toluenesulfonic acid (12 mg) are added. The reaction is refluxed for about 6 h, then it is diluted with DMF and EtOH, the catalyst is filtered on celite and the solvent is removed under reduced pressure. The crude is washed with acetone and filtered. The filtrate is concentrated and the obtained solid is purified by silica gel chromatography (eluent: CH2Cl2/EtOH=95/5) affording 50 mg of pure 2-[1-(4-chlorobenzyl)-4-(hydroxymethyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamide. The solid is crystallized from CH3CN affording 63 mg of compound with m.p. 238-240° C.

Provenance & Evidence