Sodium Sulfite → (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

Using TEMPO: A mixture of 0.96 g of the alcohol 6, 0.044 g of sodium hydrogencarbonate, 0.026 g of potassium bromide and 0.051 g of TEMPO in 3 mL of dichloromethane and 1.2 mL of water is cooled to 5° C. To the mixture is added dropwise 0.13 g of 10-13% sodium hypochlorite solution, and the mixture stirred for 5 h between 5° C. and 20° C., before addition of 0.57 g of sodium sulfite. The phases are then separated and the organic phase washed twice with 5 mL of water. Evaporation of the solvent in vacuum affords e.g. 0.50 g of the aldehyde 7 as an oil.

Provenance & Evidence