Sodium hydride → (S)-5,11-Dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (80% dispersion in oil, 40 mg) was added to a solution of 5,11-dihydrodibenzo[b,e][1,4]thiazepine (see Example 1 for source) (213 mg) in dimethylformamide (10 ml) and the mixture heated at 60° C. for 45 minutes, treated with a solution of (S)-1-(4-methylphenylsulphonyl)-2-(4-methylphenylsulphonyloxymethyl)pyrrolidine (see Preparation 15 for source) (440 mg) in dimethylformamide (5 ml), heated at 60° C. for 7 hours and evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water and the organic layer washed with water, dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, performing a gradient elution initially using hexane as eluant and changing to hexane/ethyl acetate (60:40). Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil, (50 mg, 24%).

Provenance & Evidence