Potassium Carbonate → tert-Butyl 3-ethynylpyrrolidine-1-carboxylate

Participants

Reaction Steps

Dimethyl-1-diazo-2-oxypropylphosphonate (11.5 g, 60 mmol) was added to a solution of tert-butyl 3-formylpyrrolidine-1-carboxylate (10 g, 50 mmol) and potassium carbonate (13.8 g, 100 mmol) in dry methanol (150 mL). After 16 hours, the reaction mixture was filtered and washed with methanol. The filtrate was extracted with diethyl ether, and the organic layer was washed with 5% aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford tert-butyl 3-ethynylpyrrolidine-1-carboxylate.

Provenance & Evidence