Tetrahydrofuran → (S)-3-(1-Hydroxyprop-2-ynyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Participants

Reaction Steps

0.5 M Ethynylmagnesium bromide in THF (6.3 mL, 3140 μmol) was added dropwise over 5 minutes to a stirred solution of (S)-3-formylpyrrolidine-1-carboxylic acid t-butyl ester (0.5 g, 2 mmol) in THF (5 mL, 60 mmol) at 0° C. The mixture was allowed to warm to room temperature. After 4 hours, the reaction was quenched with the addition of saturated aqueous NH4Cl (10 mL) and extracted with EtOAc (2×10 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo.

Provenance & Evidence