[(2S)-5-oxopyrrolidin-2-yl]methyl methanesulfonate

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

Procedure: To a solution of (5S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.69 mmol) in dichloromethane (40 mL) at 0° C. was added triethylamine (1.816 mL, 13.03 mmol) followed by dropwise addition of methanesulfonyl chloride (0.812 mL, 10.42 mmol). The resulting mixture was stirred at room temperature for two hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as a colorless, waxy solid (1.68 g, quantitative). it was partitioned between water and dichloromethane (3×) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo

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

Procedure: To a solution of (5S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.69 mmol) in dichloromethane (40 mL) at 0° C. was added triethylamine (1.816 mL, 13.03 mmol) followed by dropwise addition of methanesulfonyl chloride (0.812 mL, 10.42 mmol). The resulting mixture was stirred at room temperature for two hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as a colorless, waxy solid (1.68 g, quantitative). it was partitioned between water and dichloromethane (3×) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo

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

Procedure: To a solution of (5S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.69 mmol) in dichloromethane (40 mL) at 0° C. was added triethylamine (1.816 mL, 13.03 mmol) followed by dropwise addition of methanesulfonyl chloride (0.812 mL, 10.42 mmol). The resulting mixture was stirred at room temperature for two hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as a colorless, waxy solid (1.68 g, quantitative). it was partitioned between water and dichloromethane (3×) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo

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

Procedure: To a solution of (5S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.69 mmol) in dichloromethane (40 mL) at 0° C. was added triethylamine (1.816 mL, 13.03 mmol) followed by dropwise addition of methanesulfonyl chloride (0.812 mL, 10.42 mmol). The resulting mixture was stirred at room temperature for two hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as a colorless, waxy solid (1.68 g, quantitative). it was partitioned between water and dichloromethane (3×) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (+)-methanesulfonic acid (S)-5-oxo-pyrrolidin-2-ylmethyl ester (500 mg, 2.59 mmol) and 2-(benzylamino)ethanol (1.56 g, 10.36 mmol) was heated at 130° C. in a microwave oven (Personal Chemistry Emrys™ Optimizer) for 40 minutes. The residue was partitioned between water and DCM, the organic phase was washed with brine, dried (Na2SO4) and evaporated under vacuum. The crude was purified by flash chromatography (DCM/MeOH from 95/5 to 90/10 respectively) to afford the title compound as yellow oil (620 mg, 96% yield). The residue was partitioned between water and DCM the organic phase was washed with brine dried (Na2SO4) evaporated under vacuum The crude was purified by flash chromatography (DCM/MeOH from 95/5 to 90/10 respectively)

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

Procedure: To a solution of commercially available (S)-(+)-5-(hydroxymethyl)pyrrolidin-2-one (2 g, 17.36 mmol) in ethanol-free CHCl3 (60 ml), triethylamine (TEA) (2.63 g, 26.04 mmol) and methanesulfonyl chloride (2.38 g, 20.84 mmol) were added dropwise at 0° C. The mixture was left stirring at room temperature for 3 hours, then it was diluted with dichloromethane (DCM) (60 ml) and washed with a saturated aqueous solution of NaHCO3 (3×30 ml). After drying (Na2SO4) the solvent was removed under reduced pressure and the residue was purified by flash chromatography (DCM/MeOH 9/1 respectively) to give the title compound as a pale yellow solid (2.2 g, 65% yield). The mixture was left washed with a saturated aqueous solution of NaHCO3 (3×30 ml) After drying (Na2SO4) the solvent was removed under reduced pressure the residue was purified by flash chromatography (DCM/MeOH 9/1 respectively)

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

Procedure: To a solution of (5S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.69 mmol) in dichloromethane (40 mL) at 0° C. was added triethylamine (1.816 mL, 13.03 mmol) followed by dropwise addition of methanesulfonyl chloride (0.812 mL, 10.42 mmol). The resulting mixture was stirred at room temperature for two hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as a colorless, waxy solid (1.68 g, quantitative). it was partitioned between water and dichloromethane (3×) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo

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

Procedure: To a solution of (5S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.69 mmol) in dichloromethane (40 mL) at 0° C. was added triethylamine (1.816 mL, 13.03 mmol) followed by dropwise addition of methanesulfonyl chloride (0.812 mL, 10.42 mmol). The resulting mixture was stirred at room temperature for two hours, and then it was partitioned between water and dichloromethane (3×). The organic extracts were combined and dried over Na2SO4, the drying agent was removed by filtration, and the solution was concentrated in vacuo to give the title compound as a colorless, waxy solid (1.68 g, quantitative). it was partitioned between water and dichloromethane (3×) dried over Na2SO4 the drying agent was removed by filtration the solution was concentrated in vacuo