Water → trans-1-(2-Hydroxymethylanilino)-2-methylaminoindane

Participants

Reaction Steps

A solution of trans 1-(2-methoxycarbonylanilino)-2-ethoxycarbonylaminoindane (1.73 kg; 4.9 moles) in diethyl ether (36 l) was added dropwise to a suspension of lithium aluminum hydride (900 g; 23.7 moles) in diethyl ether (28 l), under nitrogen, over a period of ca 1.5 h. After stirring overnight at room temperature the excess lithium aluminium hydride was carefully decomposed with water (2.5 l), and 10% sodium hydroxide (30 l) and water (5 l) was added. The organic layer was separated and the aqueous phase extracted with two further portions of ether (2×20 l). The combined extracts were washed (water), dried (MgSO4) and concentrated. Crystallisation from ethyl acetate/pet. ether afforded the title compound (1.17 Kg; 89%) m.p. 113°-4°.

Provenance & Evidence