1-(4-hydroxyiminopiperidin-1-yl)-2,2-dimethylpropan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 3.0 g (16 mmol) of the N-trimethylacetyl-4-piperidone obtained according to the procedure above and 1.2 g (17 mmol) of hydroxylamine hydrochloride were placed into a 50 mL flask with 20 mL of ethanol. To the resulting mixture was added 1.9 g (18 mmol) of Na2CO3, and the resulting mixture was allowed to stir at room temperature overnight. The ethanol was removed in vacuo, and the resulting solid was triturated with ethyl acetate (2×50 mL). Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL), and dried (Na2SO4). The ethyl acetate solution was concentrated to yield 2.4 g (74%) of N-trimethylacetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.75 (dd, 4H, J=12.3, 6.2 Hz), 2.68 (dd, 2H, J=6.2, 6.2 Hz), 2.39 (dd, 2H, J=6.2, 6.1 Hz), 1.36 (s, 9H); 13C NMR (75 MHz, CDCl3) δ176.66, 156.34, 45.02, 43.51, 38.77, 31.13, 28.31, 24.93. The ethanol was removed in vacuo the resulting solid was triturated with ethyl acetate (2×50 mL) Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL) dried (Na2SO4) The ethyl acetate solution was concentrated

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

Procedure: 3.0 g (16 mmol) of the N-trimethylacetyl-4-piperidone obtained according to the procedure above and 1.2 g (17 mmol) of hydroxylamine hydrochloride were placed into a 50 mL flask with 20 mL of ethanol. To the resulting mixture was added 1.9 g (18 mmol) of Na2CO3, and the resulting mixture was allowed to stir at room temperature overnight. The ethanol was removed in vacuo, and the resulting solid was triturated with ethyl acetate (2×50 mL). Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL), and dried (Na2SO4). The ethyl acetate solution was concentrated to yield 2.4 g (74%) of N-trimethylacetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.75 (dd, 4H, J=12.3, 6.2 Hz), 2.68 (dd, 2H, J=6.2, 6.2 Hz), 2.39 (dd, 2H, J=6.2, 6.1 Hz), 1.36 (s, 9H); 13C NMR (75 MHz, CDCl3) δ176.66, 156.34, 45.02, 43.51, 38.77, 31.13, 28.31, 24.93. The ethanol was removed in vacuo the resulting solid was triturated with ethyl acetate (2×50 mL) Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL) dried (Na2SO4) The ethyl acetate solution was concentrated

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

Procedure: 3.0 g (16 mmol) of the N-trimethylacetyl-4-piperidone obtained according to the procedure above and 1.2 g (17 mmol) of hydroxylamine hydrochloride were placed into a 50 mL flask with 20 mL of ethanol. To the resulting mixture was added 1.9 g (18 mmol) of Na2CO3, and the resulting mixture was allowed to stir at room temperature overnight. The ethanol was removed in vacuo, and the resulting solid was triturated with ethyl acetate (2×50 mL). Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL), and dried (Na2SO4). The ethyl acetate solution was concentrated to yield 2.4 g (74%) of N-trimethylacetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.75 (dd, 4H, J=12.3, 6.2 Hz), 2.68 (dd, 2H, J=6.2, 6.2 Hz), 2.39 (dd, 2H, J=6.2, 6.1 Hz), 1.36 (s, 9H); 13C NMR (75 MHz, CDCl3) δ176.66, 156.34, 45.02, 43.51, 38.77, 31.13, 28.31, 24.93. The ethanol was removed in vacuo the resulting solid was triturated with ethyl acetate (2×50 mL) Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL) dried (Na2SO4) The ethyl acetate solution was concentrated

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 3.0 g (16 mmol) of the N-trimethylacetyl-4-piperidone obtained according to the procedure above and 1.2 g (17 mmol) of hydroxylamine hydrochloride were placed into a 50 mL flask with 20 mL of ethanol. To the resulting mixture was added 1.9 g (18 mmol) of Na2CO3, and the resulting mixture was allowed to stir at room temperature overnight. The ethanol was removed in vacuo, and the resulting solid was triturated with ethyl acetate (2×50 mL). Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL), and dried (Na2SO4). The ethyl acetate solution was concentrated to yield 2.4 g (74%) of N-trimethylacetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.75 (dd, 4H, J=12.3, 6.2 Hz), 2.68 (dd, 2H, J=6.2, 6.2 Hz), 2.39 (dd, 2H, J=6.2, 6.1 Hz), 1.36 (s, 9H); 13C NMR (75 MHz, CDCl3) δ176.66, 156.34, 45.02, 43.51, 38.77, 31.13, 28.31, 24.93. The ethanol was removed in vacuo the resulting solid was triturated with ethyl acetate (2×50 mL) Combined ethyl acetate washings were washed with water (30 mL) and brine (30 mL) dried (Na2SO4) The ethyl acetate solution was concentrated