(2S,5S)-1-(2-chloroacetyl)-5-methylpyrrolidine-2-carboxamide

Conditions: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-1-(2-Chloro-acetyl)-5-methyl-pyrrolidine-2-carboxylic acid amide (0.25 g, 1.2 mmol) and imidazole (85 mg, 1.25 mmol) ware mixed in pyridine (5 mL). The mixture was cooled to −35° C. and POCl3 (0.18 mL, 1.8 mmol) was added slowly. The mixture was stirred at −35° C. for 1 h. Saturated NH4Cl (20 mL) was added, and the mixture was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The oil was purified by flash chromatography (hexane: EtOAc, 2:1) to yield the title compound. MS (DCI) m/z 187 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic layers were dried (Na2SO4) filtered concentrated under reduced pressure The oil was purified by flash chromatography (hexane: EtOAc, 2:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic extracts were dried (Na2SO4) concentrated purified by flash chromatography (10% MeOH/EtOAc)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic extracts were dried (Na2SO4) concentrated purified by flash chromatography (10% MeOH/EtOAc)

Conditions: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-1-(2-Chloro-acetyl)-5-methyl-pyrrolidine-2-carboxylic acid amide (0.25 g, 1.2 mmol) and imidazole (85 mg, 1.25 mmol) ware mixed in pyridine (5 mL). The mixture was cooled to −35° C. and POCl3 (0.18 mL, 1.8 mmol) was added slowly. The mixture was stirred at −35° C. for 1 h. Saturated NH4Cl (20 mL) was added, and the mixture was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The oil was purified by flash chromatography (hexane:EtOAC, 2:1) to yield the title compound. MS (DCI) m/z 187 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic layers were dried (Na2SO4) filtered concentrated under reduced pressure The oil was purified by flash chromatography (hexane:EtOAC, 2:1)

Conditions: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-1-(2-Chloro-acetyl)-5-methyl-pyrrolidine-2-carboxylic acid amide (0.25 g, 1.2 mmol) and imidazole (85 mg, 1.25 mmol) ware mixed in pyridine (5 mL). The mixture was cooled to −35° C. and POCl3 (0.18 mL, 1.8 mmol) was added slowly. The mixture was stirred at −35° C. for 1 h. Saturated NH4Cl (20 mL) was added, and the mixture was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The oil was purified by flash chromatography (hexane:EtOAC, 2:1) to yield the title compound. MS (DCI) m/z 187 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic layers were dried (Na2SO4) filtered concentrated under reduced pressure The oil was purified by flash chromatography (hexane:EtOAC, 2:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic extracts were dried (Na2SO4) concentrated purified by flash chromatography (10% MeOH/EtOAc)

Conditions: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-1-(2-Chloro-acetyl)-5-methyl-pyrrolidine-2-carboxylic acid amide (0.25 g, 1.2 mmol) and imidazole (85 mg, 1.25 mmol) ware mixed in pyridine (5 mL). The mixture was cooled to −35° C. and POCl3 (0.18 mL, 1.8 mmol) was added slowly. The mixture was stirred at −35° C. for 1 h. Saturated NH4Cl (20 mL) was added, and the mixture was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The oil was purified by flash chromatography (hexane:EtOAC, 2:1) to yield the title compound. MS (DCI) m/z 187 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic layers were dried (Na2SO4) filtered concentrated under reduced pressure The oil was purified by flash chromatography (hexane:EtOAC, 2:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic extracts were dried (Na2SO4) concentrated purified by flash chromatography (10% MeOH/EtOAc)

Conditions: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-1-(2-Chloro-acetyl)-5-methyl-pyrrolidine-2-carboxylic acid amide (0.25 g, 1.2 mmol) and imidazole (85 mg, 1.25 mmol) ware mixed in pyridine (5 mL). The mixture was cooled to −35° C. and POCl3 (0.18 mL, 1.8 mmol) was added slowly. The mixture was stirred at −35° C. for 1 h. Saturated NH4Cl (20 mL) was added, and the mixture was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The oil was purified by flash chromatography (hexane:EtOAc, 2:1) to yield the title compound. MS (DCI) m/z 187 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic layers were dried (Na2SO4) filtered concentrated under reduced pressure The oil was purified by flash chromatography (hexane:EtOAc, 2:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic extracts were dried (Na2SO4) concentrated purified by flash chromatography (10% MeOH/EtOAc)

Conditions: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-1-(2-Chloro-acetyl)-5-methyl-pyrrolidine-2-carboxylic acid amide (0.25 g, 1.2 mmol) and imidazole (85 mg, 1.25 mmol) ware mixed in pyridine (5 mL). The mixture was cooled to −35° C. and POCl3 (0.18 mL, 1.8 mmol) was added slowly. The mixture was stirred at −35° C. for 1 h. Saturated NH4Cl (20 mL) was added, and the mixture was extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The oil was purified by flash chromatography (hexane: EtOAc, 2:1) to yield the title compound. MS (DCI) m/z 187 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic layers were dried (Na2SO4) filtered concentrated under reduced pressure The oil was purified by flash chromatography (hexane: EtOAc, 2:1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+. the mixture was extracted with EtOAc (3×) The combined organic extracts were dried (Na2SO4) concentrated purified by flash chromatography (10% MeOH/EtOAc)