Water → Phenethylamine, N-butyl-alpha,alpha-dimethyl-

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Reaction Steps

To a solution of compound D-3-7 (100 g, 380 mmol) and Et3N (76.8 g, 760 mmol) in dichloromethane (1.5 L), cooled to 0° C., is added triflic anhydride (Tf2O) (107.0 g, 380 mmol) via an addition funnel. Upon complete addition of Tf2O the solution is then warmed to room temperature for 5 h. The reaction mixture is then treated with H2O and dichloromethane and the organic phase is separated. The organic phase is washed with brine and dried over anhydrous Na2SO4. The mixture is then filtered and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography (using 20:1 petroleum ether:EtOAc) to provide compound D-3-8 (105 g, 70% yield).

Provenance & Evidence