tert-butyl (2R,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetrabutyl ammonium fluoride (16.7 mL, 1N in THF, 16.73 mmol) was added to a solution of 1,1-dimethylethyl(2R,3S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-1-pyrrolidinecarboxylate in THF and stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to yield the title compound (1.55 g, 7.8 mmol). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.0 (m, 3 H) 1.4 (s, 9 H) 1.6 (m, 1 H) 1.9 (m, 1 H) 3.3 (m, 2 H) 3.5 (m, 1 H) 3.8 (m, 1 H) 4.9 (s, 1 H). ES+=202.15. The reaction mixture was concentrated under reduced pressure purified by silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Tetrabutyl ammonium fluoride (16.7 mL, 1N in THF, 16.73 mmol) was added to a solution of 1,1-dimethylethyl(2R,3S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methyl-1-pyrrolidinecarboxylate in THF and stirred for 16 hours at room temperature. The reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to yield the title compound (1.55 g, 7.8 mmol). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.0 (m, 3H), 1.4 (s, 9H), 1.6 (m, 1H), 1.9 (m, 1H), 3.3 (m, 2H), 3.5 (m, 1H), 3.8 (m, 1H), 4.9 (s, 1H). ES+=202.15. The reaction mixture was concentrated under reduced pressure purified by silica gel column chromatography