HCID 23003909, compound → HCID 23003927, compound

Participants

Reaction Steps

A mixture of dimethyl 3-(1-boc-2,3-dihydro-1H-indol-5-yl)-2-methoxycarbonyl-pentanedioate [530 mg, Reference Example 10(a)] and concentrated hydrochloric acid (20 ml) was stirred at reflux overnight then evaporated. The residual clear foam (370 mg) was treated with methanol (20 ml), then with concentrated sulphuric acid (10 drops). The resulting solution was stirred at reflux for 2 hours then evaporated. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer and extracts were washed with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petrol (1:1, v/v) to give the title compound (150 mg) as a clear oil. MS (ES+) 278 (MH+).

Provenance & Evidence