Water → HCID 10883437, compound

Participants

Reaction Steps

Methyl 3-(4-benzyloxyphenyl)-4-ethylpyrrolo[2,1,5-cd]indolizine-1-carboxylate (8.5 g, 20.8 mmol) was dissolved in 170 ml of dry tetrahydrofurane under a nitrogen atmosphere. Lithium aluminium hydride (1.24 g, 32.6 mmol) was added in portions and stirring was continued for 21/2 hours. Water (10 ml) was added dropwise, and 95 ml of saturated aqueous potassium carbonate and 200 ml of diethyl ether was added. The organic layer was separated, and the aqueous layer was extracted with diethyl ether (2×300 ml). The combined organic layers were washed with 200 ml of water and dried over sodium hydrogen carbonate. The solvent was evaporated and the remaining product was dried to afford 7.7 g (97%) of the title compound as yellow crystals. M.p. 148-150° C. MS(SP): m/z 381 (M+). 1H-NMR (CDCl3, 300 MHz) δ: 1.48 (t, 3H); 3.23 (q, 2H); 5,17 (s, 2H); 5.18 (s, 2H); 7.14 (d, 2H); 7.32-7.52 (m, 5H); 7.57 (s, 1H); 7.65 (t, 1H); 7.72 (d, 2H); 7.92 (d, 1H); 8.02 (d, 1H).

Provenance & Evidence