Triethylamine → (RS)-4-[1-(4-phenyl-butyl)-pyrrolidine-3-sulfonyl]-phenol hydrochloride

Participants

Reaction Steps

(RS)-4-(Pyrrolidine-3-sulfonyl)-phenol trifluoroacetic acid salt (0.22 g, 0.65 mmol), 4-phenyl-butyraldehyde (0.096 g, 0.65 mmol), triethylamine (0.090 ml., 0.65 mmol), and sodium triacetoxyborohydride (0.2 g, 0.97 mmol) were suspended in 1,2-dichloroethane (4 ml). After 3 hours stirring at room temperature, the reaction mixture was quenched with saturated NaHCO3 (10 ml). The aqueous phase was extracted with CH2Cl2 (3 times). The combined organic phases were dried over Na2SO4, filtered and the solvent was evaporated. The residue was chromatographed over silica gel (CH2Cl2—MeOH, 19:1) to provide a white solid which was suspensed in MeOH. HCl-Et2O was added to provide (RS)-4-[1-(4-phenyl-butyl)-pyrrolidine-3-sulfonyl]-phenol hydrochloride (0.180 g, 70%) as a white solid, m.p. 121-124° C. and MS: m/e=360.3 (M+H+).

Provenance & Evidence