tert-Butylsulfinamide, (R)-(+)- → HCID 90200305, compound

Participants

Reaction Steps

To a solution of 5-bromo-2-fluoronicotinaldehyde (5 g, 24.51 mmol) and titanium (IV) ethoxide (15.42 ml, 73.5 mmol) in DCM (49.0 mL) was added (R)-2-methylpropane-2-sulfinamide (3.12 g, 25.7 mmol). The reaction mixture was then stirred at rt for 48 h. After 48 h, the reaction mixture was poured into brine at rt while rapidly stirring the mixture. The resulting suspension was filtered through a plug of CELITE®, and the filter cake was washed several times with DCM. The filtrate were separated, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give 7.6 g of crude product which was further purified using silica gel chromatography to yield the desired product (6.97 g, 93%) as an off white solid. MS (ESI) m/z: 330.8 (M+Na)+.

Provenance & Evidence