[N:1]([C@H:4]1[C@H:8]([OH:9])[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)=[N+:2]=[N-:3].C(=O)([O-])[O-].[K+].[K+]>C(O)(C(F)(F)F)=O.ClCCl.CO.ClCCl>[N:1]([C@@H:4]1[CH2:5][NH:6][CH2:7][C@H:8]1[OH:9])=[N+:2]=[N-:3](3R,4R)-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate (3.6 g, 16.0 mmol) was stirred in 10% TFA in dichloromethane (100 mL) for 2 hours. The mixture was concentrated under reduced pressure and the residue obtained dissolved in a 10% MeOH/dichloromethane solution (50 mL) and treated with potassium carbonate (20 g) and the suspension stirred at ambient temperature for 2 hours, then filtered through a pad of Celite and washed with 10% MeOH: dichloromethane. The filtrate was concentrated to afford (3R,4R)-4-azidopyrrolidin-3-ol in quantitative yield.
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