tert-Butylsulfinamide, (R)-(+)-

Usessuzuki reaction, useful reagent for synthesizing chiral amines.

UsesChiral ligand used in pharmaceutical compositions

Uses(R)-(+)-2-Methyl-2-propanesulfinamide is a chiral ligand, which is used in pharmaceutical compositions. Further, it is used in the preparation of beta-chloro sulfinamides in the synthesis of chiral azridines. It is involved in the preparation of organocatalyst for enantioselective reduction of imines. It serves as a reagent for synthesizing chiral amines. In addition to this, it is converted into P,N-sulfinyl imine ligands through condensation with aldehydes and ketones which undergoes iridium-catalyzed asymmetric hydrogenation of olefins.

PreparationAcetic acid (70 g), R-tert-butylsulfinylhydrazine (42 g), zinc powder (60.5 g) and dichloromethane (150 mL) were added to the reaction flask. The temperature was slowly heated to 35-42 °C . After 16 hours, the filtrate was poured into 70 mL water. Dichloromethane (75 g×5) was added for extraction. Collected the organic phase, added 48% NaOH to adjust ρΗ (7-8). Then added NaCl, the layers were separated and the organic phase was washed with 15 g saturated aqueous solution of sodium chloride. The solution was dried over magnesium sulfate. After filterED, filtrate was concentrated under reduced pressure at 25-30 °C until no slipping. N-heptane was replaced, 28 g mixed solvent of N-heptane and toluene (N-heptane: toluene = 6:1) were added to perform beating at low temperature, filtered to obtain (R)-(+)-2-Methyl-2-propanesulfinamide. Yield=83%