Water → benzyl (3R,4R)-3-amino-4-fluoropyrrolidine-1-carboxylate

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Reaction Steps

To a stirred solution of (trans)-benzyl 3-azido-4-fluoropyrrolidine-1-carboxylate (30 g, 0.114 mol) in THF (0.3 L) was added PPh3 (33 g, 0.126 mol) portion wise at 0-5° C. The resulting mixture was then warmed to rt and stirred for 2 hr. 30 mL of water was then added and the resulting mixture was heated to reflux overnight. The reaction mixture was concentrated and the residue diluted with EtOAc (0.2 L) and extracted with sat. citric acid (4×100 mL). The combined aqueous extracts were washed with EtOAc (3×50 mL), then adjusted pH to 8 with sat. aq. K2CO3, and extracted with DCM (4×100 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4, concentrated, then dried in vacuo to give the title compound as light yellow oil that solidified on standing to afford an off-white solid (16 g, 59% yield).

Provenance & Evidence