Diethyl Ether → (3-{[2-(Dimethylamino)ethyl]oxy}phenyl)methanol

Participants

Reaction Steps

Methyl 3-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoate (for a preparation see Intermediate 16) (2.22 g, 9.36 mmol) was dissolved in THF (15 mL) and cooled in ice. The solution was then treated dropwise with an ether solution of LiAlH4 (1M, 10 mL) under nitrogen, and the mixture was stirred in an ice-bath for 1.5 h. LCMS indicated only completion. The mixture was cooled in ice and aqueous saturated sodium sulfate solution was added until a white precipitate formed. The mixture was stirred for 2 h and then allowed to stand O/W at RT. The mixture was then filtered, the solid was washed with ethyl acetate, and the filtrate and washings concentrated under reduced pressure. The resulting colourless oil was dissolved in methanol and applied to a pre-washed SCX-2 cartridge. The cartridge was washed with methanol and then eluted with 10% aqueous ammonia in methanol. The ammoniacal fractions were combined and evaporated under reduced pressure to give the title compound (1.236 g, 68%). LCMS (System A) RT=0.36 min, ES+ve m/z 196 (M+H)+.

Provenance & Evidence