Acetic Acid → 2-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1lambda6-isothiazolidine-3-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)—N,N′-dimethyl-3-phenyl-propane-1,2-diamine (120 mg, 0.673 mmol) in methanol (2 mL) under argon was added a solution of 2-(3-formyl-benzyl)-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid ethyl ester (Intermediate 4; 230.5 mg, 0.740 mmol) in methanol (4 mL). The solution was cooled 0° C. in an ice bath and to this was added sodium cyanoborohydride (63.4 mg, 1.01 mmol) and acetic acid (0.3 mL). The solution was allowed to warm to room temperature and stirred for 16 h under argon. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (2×10 mL) and the aqueous layer was extracted with ethyl acetate (50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to give crude 2-{3-[((S)-1-dimethylaminomethyl-2-phenyl-ethylamino)-methyl]-benzyl}-1,1-dioxo-1λ6-isothiazolidine-3-carboxylic acid ethyl ester (360 mg) as colorless oil.

Provenance & Evidence