Dimethylamine → tert-Butyl (3R)-6-cyclohexyl-3-{3-[(dimethylamino)carbonyl]-1,2,4-oxadiazol-5-yl}hexanoate

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Reaction Steps

A solution of ethyl 5{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]4-cyclohexylbutyl)-1,2,4-oxadiazole-3-carboxylate (Preparation 3) (1.00 g, 2.53 mmol) in ethanol (8 ml) was cooled to 0° C. and treated dropwise with dimethylamine (5.6M in ethanol, 4.50 ml, 25.3 mmol). The solution was stirred for 17 hours being allowed to warm up to room temperature over this time. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:ethyl acetate (4:1) to afford the title compound as a yellow oil (0.93 g).

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