Water → HCID 131725217, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-N-(2,5-dichlorophenyl)-N-[(R)-1-methyl-3-azidopropyl]benzenesulfonamide (0.941 g, 2.16 mmol) in THF (21 mL) was added lithium aluminum hydride (4.33 mL, 1 M in THF) at 0° C. under nitrogen atmosphere. The resulting mixture was allowed to stir at 0° C. for 1 h and subsequently treated by successive dropwise addition of 0.165 mL of water, 0.165 mL of 15% sodium hydroxide solution, and 0.493 mL of water. The mixture was filtered and concentrated under reduced pressure. Silica gel chromatography (3:10 ethyl acetate:hexanes) of the concentrate afforded 0.748 g of 4-chloro-N-2,5-dichlorophenyl)-N-[(R)-1-methyl-3-aminopropyl]benzenesulfonamide as a light brown oil in 85% yield.

Provenance & Evidence