Methanamine, N-methoxy-, hydrochloride (1:1) → (3R,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid methoxy-methyl-amide

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Reaction Steps

To a suspension of N,O-dimethylhydroxylamine hydrochloride (3.61 g, 0.037 mol) in DCM (40 mL) at RT was added trimethylaluminium (2.0M solution in heptane, 18.5 ml, 0.037 mol) dropwise and stirring was continued for one hour. To this mixture was added a solution of (S)-4-benzyl-3-[(3R,4S)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carbonyl]-oxazolidin-2-one (9.47 g, 0.0186 mol) in DCM (50 mL) over 10 minutes. Stirring was continued for three hours. The reaction was quenched by an addition of aq. Potassium sodium tartarate solution and extracted with ethyl acetate. The separated organic layer was washed with brine and dried on Na2SO4 and concentrated under vacuo. Purification by column chromatography (SiO2, EtOAc/H, 2:3) yielded 6.58 g (90%) of the title compound as a light yellow oil. ES-MS m/e: 393.1 (M+H+).

Provenance & Evidence