Dimethylformamide → (RS)-4-[1-(4-m-tolyl-butyl)-pyrrolidine-3-sulfonyl]-phenol

Participants

Reaction Steps

To a 0° C. solution of (RS)-4-(1-but-3-enyl-pyrrolidine-3-sulfonyl)-phenol (0.106 g, 0.378 mmol) in THF (0.5 ml), 9-BBN (1.66 ml, 0.74 ml, 0.5 M solution in THF) was added dropwise. The reaction mixture was allowed to warm up slowly to room temperature. After 4 hours stirring, the reaction mixture was treated successively with DMF (1.5 ml), 3-bromotoluene (0.046 ml, 0.377 mmol), PdCl2(dppf)2-dichloromethane complex (9.3 mg, 0.01 mmol), and K2CO3 (95 mg, 0.69 mmol). After 5 hours stirring at 60° C., the reaction mixture was cooled to room temperature, quenched with ethylacetate and H2O. The aqueous phase was extracted with ethylacetate. The combined organic phases were washed with H2O, dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel (CH2Cl2—MeOH, 98:2) to provide (RS)-4-[1-(4-m-tolyl-butyl)-pyrrolidine-3-sulfonyl]-phenol (66 mg, 47%) as a light yellow foam, MS: m/e=374.4 (M+H+).

Provenance & Evidence