Aluminium lithium hydride → HCID 23047401, compound

Participants

Reaction Steps

A solution of ethyl 3-isopropyl-1-phenylpyrrolo-[2,1-a]isoquinoline-2-carboxylate (6.25 g) in anhydrous diethyl ether (100 ml) was added to a stirred suspension of lithium aluminum hydride (2.7 g) in diethyl ether (160 ml) at -2° C. under an atmosphere of argon. The mixture was stirred at between -5° and 0° C. for 5 hours and then the reaction mixture was quenched by the dropwise addition of ethyl acetate (50 ml), followed by dilute hydrochloric acid (100 ml; 1N), maintaining the temperature below 10° C. The organic phase was then separated. The aqueous phase was extracted with dichloromethane (2×150 ml) and the organic solutions were combined, washed with brine (300 ml), dried over magnesium sulphate and evaporated, to give 2-hydroxymethyl-3-isopropyl-1-phenylpyrrolo[2,1-a]-isoquinoline (5.1 g) in the form of a sticky yellow solid. [N.M.R. (in DMSO-d6): 1.48 (6H, d, J= 7 Hz), 3.65 (1H, septet, J=7 Hz), 4.3 (2H, d, J=4 Hz), 4.5 (1H, broad t, J=4 Hz), 6.85 (1H, d, J=8 Hz), 7.0-7.7 (9H, m), and 8.1 (1H, d, J=8 Hz)].

Provenance & Evidence