Proton sponge → HCID 57686422, compound

Participants

Reaction Steps

To 1-benzyl-3-methylsulfanyl-pyrrolidine-3-carboxylic acid methyl ester 8BP (131 g, 493.7 mmol) dissolved in dichloroethane (2.6 L) at 0° C. was added N,N,N′,N′-Tetramethyl-naphthalene-1,8-diamine 9BP (31.8 g, 0.144 mmol) and then 2-Chloropropionyl chloride 10BP (64 mL, 593.1 mmol) sequentially. The reaction mixture was stirred for one overnight at ambient temperature and then concentrated to dryness. The residue was dissolved in 2.8 L of methanol and refluxed at 65° C. for 3.5 h. The reaction mixture was then concentrated to dryness and the residue was purified by column chromatography on silica gel eluting with a solution of methanol in dichloromethane (1:9) to give 3-Methylsulfanyl-pyrrolidine-3-carboxylic acid methyl ester 4BP (75 g, 86%).

Provenance & Evidence