Toluene → HCID 86705520, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 248 (2.0 g, 7.3 mmol) and toluene (30 mL) cooled to −78° C. was added (3,4-dichlorophenyl)magnesium bromide (29 mL, 15 mmol) and warmed to 0° C. for 30 min. The reaction was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (4:1 to 1:1) to afford 1.8 g (59%) of (S)—N—((S)-(3,4-dichlorophenyl)((S)-1,4-dioxaspiro[4.5]decan-2-yl)methyl)-2-methylpropane-2-sulfinamide (250) which appears to be a ca. 10:1 mixture of diastereomers by 1H NMR.

Provenance & Evidence