Dimethyl Sulfoxide → (2R,3S,5S)-5-Formyl-3-isopropyl-2-[4-methoxy-3-(3 methoxy-propoxy)-phenyl]pyrrolidine-1-carboxylic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

Alternatively, to a solution of 1.1 g of the alcohol 6 in 10 mL of dichloromethane is added 0.4 g of pyridine, 1.1 g of diisopropylethylamine and 2.0 g of dimethyl sulfoxide. The mixture is cooled to −5° C. and 0.6 g of sulfur trioxide-pyridine complex is added in four portions over a period of 2 h. The reaction is quenched by addition of 2.5 mL of water and acidified by addition of 1 mL of 37% hydrochloric acid. The phases are separated and the organic phase washed with 2.5 mL of water, dried over sodium sulfate and the solvent removed in-vacuum, to afford e.g. 0.88 g of the aldehyde 7 as an oil.

Provenance & Evidence