Triethylamine → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

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Reaction Steps

A solution of 31.4 g (144 mmol) di-tert-butyl dicarbonate in dichloromethane was added to a solution of 14.6 g (144 mmol) L-prolinol and 22.1 ml (159 mmol) triethyl amine in dichloromethane at 0° C. The reaction was left overnight at rt. The dichloromethane phase was washed with 30% citric acid aq, saturated NaCl aq and saturated NaHCO3 aq. The organic phase was dried with Na2SO4 and evaporated. Yield 27.71 g (138 mmol, 96%). 27.71 g (138 mmol) BOC-L-prolinol was oxidized to the corresponding aldehyde according to procedure G. Yield of crude product 22.63 g. The product was purified with a silica column using 20% ethyl acetate in petroleum ether as eluent. Yield 18.4 g (92 mmol, 67%).

Provenance & Evidence