Aluminium lithium hydride → 3-Dibenzylaminocyclohexylmethanol

Participants

Reaction Conditions

Reaction Steps

At 0° C., 23 g of a 1:3.5 mixture of methyl 3-dibenzylaminocyclohexanoate and benzyl 3-dibenzylaminocyclohexanoate were added dropwise to a suspension of 4.4 g of LiAlH4 in 250 ml of diethyl ether. The suspension was stirred at 0° C. for 2 h and then quenched using 2 ml of EtOAc, and 10 ml of 10N KOH were added. 50 g of MgSO4 were then added and the suspension was filtered. The residue was digested with EtOAc for 2 h and filtered again. The filtrate was concentrated, giving the product as an oil. C21 H27NO (309.46), LCMS (ESI): 310.2 (MH+).

Provenance & Evidence