Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate → (+/-)Methyl 4-[5-(2-cyclopentylacetamido)-1-ethyl-2,3-dihydroindol-3-ylmethyl]-3-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

Palladium-on-carbon (10% w/w, 0.5 g.) was added to a mixture of methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate (0.5 g., prepared as described in Example 80), and formic acid (99%, 20 ml.), under an atmosphere of nitrogen. The mixture was vigorously stirred and heated at 80° C. for one hour. The cooled mixture was filtered through a pad of diatomaceous earth, the filter cake washed with methanol, and the filtrate evaporated. The resulting oil was dissolved in ethyl acetate (30 ml.) washed with water, brine, then dried (MgSO4) and evaporated. The product was purified by flash chromatography on silica gel (4 cm. diameter column), eluting with 2:3 v/v ethyl acetate:hexane, to give the title compound (0.37 g., 80%) as a foam; NMR (250 MHz, DMSO-d6): 1.04 (t,3 H, --CH2C/e,uns/H/ 3); 1.15 (m,2 H, cyclopentyl ring); 1.4-1.8 (m,6 H, cyclopentyl ring); 2.2 (m,3 H); 2.7 (dd,1 H); 2.85-3.25 (m,5 H); 3.45 (m,1 H); 3.86 (s,3 H, OCH3); 3.87 (s,3 H, OCH3); 6.43 (d,1 H); 7.20 (m,2 H); 7.30 (d,1 H); 7.50 (m,2 H); 9.47 (s,1 H, NH).

Provenance & Evidence