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

Participants

Reaction Steps

Sodium (55 mg) was added to a solution of naphthalene (340 mg) in DME (6 ml) and the mixture stirred at room temperature for one hour, treated with a solution of (S)-5,11-dihydro-5-(1-[4-methylphenylsulphonyl]-2-pyrrolidinylmethyl)dibenzo[b,e][1,4]thiazepine (see Preparations 15 and 16) (200 mg) in DME (4 ml), stirred with ice-cooling for one hour, quenched with water and extracted with ethyl acetate. The organic extract was worked-up and purified as described in Preparation 13 to give the title compound as a colourless oil, (16 mg, 12%).

Provenance & Evidence