Diisopropylethylamine → (S)-3-((S)-2-Chloro-4-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl-benzenesulfonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

In a 50 mL round-bottomed flask, (S)-tert-butyl 3-(2-chloro-4-fluorophenylsulfonyl)-pyrrolidine-1-carboxylate, example 52D) (2 g, 5.5 mmol, 1 eq) was combined with acetonitrile (20 mL) to give a light yellow solution. (S)-octahydropyrrolo[1,2-a]pyrazine (1.04 g, 8.25 mmol, 1.5 eq) and DIEA (1.42 g, 1.92 mL, 11.0 mmol, 2 eq) were added. The reaction mixture was stirred for 15 h. The reaction mixture was heated to 60° C. and stirred for 5 h. The crude reaction mixture was concentrated in vacuo. The reaction mixture was poured into EtOAc (25 mL) and extracted with aqueous 10% Na2CO3 (2×20 mL) and brine. The organic layers were dried over Na2SO4 and concentrated in vacuo to yield a colorless viscous oil (2.48 g, 96%).

Provenance & Evidence