Water → (S)-tert-butyl 3-formylpyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-hydroxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester (21.6 g, 107 mmol, 1.0 eq.) in DCM (220 mL), was added TEMPO (300 mg, 2 mmol, 0.02 eq.) and potassium bromide (600 mg, 5 mmol, 0.05 eq.) This mixture was cooled at 0° C. and a prechilled (at 0° C.) 1:1 mixture of 0.7 M of sodium hypochlorite in water (230 mL, 1.5 eq.) and saturated, aqueous NaHCO3 (230 ml) was added drop-wise over a period of 90 minutes. The resultant mixture was extracted with DCM (3×100 mL). The combined organic layers were washed with water (2×100 mL), and then saturated aqueous NaCl (1×100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (14.6 g).

Provenance & Evidence