4-Methylmorpholine → HCID 86584830, compound

Participants

Reaction Steps

30 g (81.6 mmol) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester in 800 ml CH2Cl2 were treated with 62.8 ml (571.2, 7 eq) NMM, 2.19 g (16.24 mmol, 0.2 eq) hydroxybenzotriazole, 37.5 g (195.84 mmol, 2.4 eq) EDCI and 17.5 g (179.52 mmol, 2.2 eq) N,O-dimethylhydroxylamine-hydrochloride. The solution was stirred for 3 h at RT, concentrated and dissolved in 500 ml 1M KHSO4 solution and 500 ml EtOAc were added. The organic layer was separated and washed with brine, dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography on silica gel with EtOAc:hexane 1:1 as eluent yielding 3.6 g (62.4%) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as light yellow oil, MS: 411 (MH+).

Provenance & Evidence