Sodium Bicarbonate → Lurosetron

Participants

Reaction Steps

A solution of 6-fluoro-2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (100 mg) in N-methylpyrrolidinone (10 ml) was treated with 4-toluenesulphonic acid monohydrate (17 mg) and 4-hydroxymethyl-5-methylimidazole hydrochloride (37 mg). The mixture was then heated to 125° for 18 h during which time three further portions of 4-hydroxymethyl-5-methylimidazole hydrochloride (37 mg) were added at 1,2 and 3 h respective. The solution was then poured into 8% sodium bicarbonate solution (100 ml) and extracted with dichloromethane (3×100 ml). The combined extracts were concentrated in vacuo and the N-methylpyrrolidinone was distilled at 100°. The residue was purified by FCC eluting with System A (200:8:1) to give the title compound (100 mg), t.l.c. (System A, 100:8:1) Rf 0.3.

Provenance & Evidence