Water → 2-(Benzylthio)-3,3-dimethoxypropan-1-amine

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (13.0 g) in tetrahydrofuran (60 mL) was added dropwise a solution (76 mL) of ({[2,2-dimethoxy-1-(nitromethyl)ethyl]thio}methyl)benzene (18.6 g) in tetrahydrofuran at 0° C. The reaction mixture was warmed to room temperature, and stirred at room temperature for 1 hr. Water and 2N aqueous sodium hydroxide solution were added to the reaction mixture, and the mixture was diluted with ethyl acetate. The mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=30:70-100:0) to give the title compound (12.6 g, yield 76%) as a yellow oil.

Provenance & Evidence