Benzyltrimethylammonium hydroxide → 3-(3-1,2-Benzisoxazol-3-ylmethyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-1,2-benzisoxazol-3-ylmethyl-1,3-dihydro-benzimidazol-2-one (100 mg, 0.38 mmol) in DMF (5 ml) was added ethyl trans-2-hexenoate (80 mg, 0.57 mmol) followed by benzyltrimethylammonium hydroxide (Triton B, 40 wt % in MeOH, 17.0 ul). The resulting mixture was warmed to 60° C. for 12 h and cooled to ambient temperature. The reaction was diluted with NH4Cl (sat.) and the product was extracted into ethyl acetate (2×). The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 5% EtOAc/dichloromethane). The product-containing fractions were combined and concentrated to give 70 mg (46%) of the desired product.

Provenance & Evidence