Methylamine → HCID 178448322, compound

Participants

Reaction Steps

A stirred solution of (S)-2-((S)-1-(2-bromophenyl)but-3-enylamino)-2-phenyl-ethanol (compound 2; 124 mmol, 42.8 g) in methanol (500 mL) and methylamine (680 mmol, 71.1 mL, 33% solution in ethanol) was treated dropwise with a solution of periodic acid (340 mmol, 77 g) in methanol (50 mL) with ice/water cooling to maintain an internal temp less than 25° C. The mixture was stirred at room temperature for 3 hours then left to stand overnight. The mixture was quenched with 2M aqueous sodium hydroxide (300 mL) to give a thick precipitate that was stirred for 1 hr then the methanol was removed under vacuum. The mixture was filtered through dicalite and the gelatinous cake washed water (200 mL), then methylene chloride (250 mL) was added. Layers were separated and the aqueous layer extracted with methylene chloride (200 mL). Combined extracts dried over sodium sulfate and evaporated to give crude (S,E)-N-benzylidene-1-(2-bromo phenyl)but-3-en-1-amine (31.65 g) as a yellow oil.

Provenance & Evidence