Tetrabutylammonium Fluoride → Tert-butyl (2r,4r)-4-hydroxy-2-(methoxymethyl)pyrrolidine-1-carboxylate

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Reaction Conditions

Reaction Steps

Tetrabutyl ammonium fluoride (21.3 ml) was added to a stirred solution of tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate (6.68 g) in THF (150 ml). The resulting mixture was stirred at 20° C. for 18 hours. The reaction mixture was evaporated to dryness and the residue was purified by flash chromatography on silica eluting with increasingly polar mixtures of methanol/dichloromethane (0/100-5/95). Fractions containing the desired product were combined and evaporated to give tert-butyl (2R,4R) 4-hydroxy-2-(methoxymethyl)pyrrolidine-1-carboxylate (3.32 g) as a solid. NMR Spectrum: (DMSOd6) 1.44 (9H, s); 1.81-1.86 (1H, m); 2.05 (1H, d); 3.09 (1H, d); 3.43-3.49 (3H, s); 3.52 (3H, m); 3.83 (1H, d); 4.20-4.25 (1H, m); 4.94 (1H, d).

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