1,2-Dichloroethane → S-benzyl quinuclidine-3-carbothioate

Participants

Reaction Steps

Quinuclidine-3-carboxylic acid hydrochloride (55 mg, 0.29 mmol), EDC (83 mg, 0.43 mmol), and HOBT (65.9 mg, 0.43 mmol) were dissolved in dry THF (5 ml) under a nitrogen atmosphere. Triethylamine (140 μl, 1.00 mmol) and phenylmethanethiol (37.1 μl, 0.32 mmol) were dissolved in dry THF (2 ml) and then added to the reaction mixture. The resulting suspension was stirred at room temperature overnight. The mixture was evaporated, and the crude partitioned between EtOAc and water. The organic phase was washed with saturated NaHCO3, dried over sodium sulfate, filtered, and evaporated under vacuum to obtain S-benzyl quinuclidine-3-carbothioate (110 mg, crude), which was used in the next step without any further purification.

Provenance & Evidence