Ammonium Chloride → Methyl 6-(3,5-dimethoxypyridin-4-yl)-6-(1,1-dimethylethylsulfinamido)hexanoate

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) solution of commercially available 4-bromo-3,5-dimethoxypyridine (4.998 g; 22.92 mmol) in anh. THF (90 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (14.30 ml; 22.88 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 6-((tert-butylsulfinyl)imino)hexanoate (3.780 g; 15.28 mmol) in anh. THF (10 ml) was then added to the cooled reaction mixture, and stirring at −78° C. was continued for 60 min. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded methyl 6-(3,5-dimethoxypyridin-4-yl)-6-(1,1-dimethylethylsulfinamido)hexanoate as a yellow oil. LC-MS (conditions A): tR=0.49 min.; [M+H]+: 387.11 g/mol.

Provenance & Evidence