Triethylamine → Methyl 2-(pyrrolidin-1-ylmethyl)isonicotinate

Participants

Reaction Steps

A solution of product of stage (iii) (1.6 g) in dry dichloromethane (50 ml) at -50° was treated with triethylamine (1.07 ml) and the mixture was stirred for 5 min. A pre-cooled solution of pyrrolidine (1.28 ml) in dry dichloromethane (30 ml) was added at -60° and the mixture was stirred at -60° to 0° for 1 h and at ambient temperature for 72 h. The mixture was poured into aqueous sodium carbonate (1M; 50 ml) and the product was extracted with dichloromethane (50 ml). The organic solution was dried and evaporated leaving an oily residue (1.7 g) which was purified by flash chromatography eluting with dichloromethane/methanol/ammonia 200:10:1 to give the title compound as an oil (0.3 g).

Provenance & Evidence