HCID 90410893, compound → HCID 90410895, compound

Participants

Reaction Conditions

Reaction Steps

Into a 1000-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed oxolane (150 mL). This was followed by the addition of alumane lithium (5.6 g, 165.08 mmol, 3.35 equiv) in several batches at 0° C. To the mixture was added a solution of 2-(benzyloxy)-N,N-dimethyl-3-[(Z)-2-nitroethenyl]aniline (14.7 g, 49.27 mmol, 1.00 equiv) in tetrahtdrofuran (150 mL) dropwise with stirring at 0-10° C. The resulting solution was stirred overnight at 25° C. The mixture was cooled to 0-5° C. The reaction was then quenched by the addition of 6 mL of water, 18 mL of NaOH (10%) and 6 mL of water. The resulting solution was extracted with 2×500 mL of ethyl acetate and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (1:50-1:20). This resulted in 6.4 g (48%) of 3-(2-aminoethyl)-2-(benzyloxy)-N,N-dimethylaniline as light yellow oil. MS (ESI) m/z 271 ([M+H]+).

Provenance & Evidence