3-ethynylpiperidine

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

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

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

Procedure: To a solution of Example 10A (500 mg, 4.58 mmol) in dichloromethane (10 mL) was added triethylamine (2.55 mL, 18.32 mmol) followed by methyl chloroformate (0.532 mL, 6.87 mmol) and the mixture was stirred at room temperature for 3 hours. The mixture was diluted with water and dichloromethane and the organic layer was separated and washed with water and brine. After drying over sodium sulfate, filtration, and concentration, the residue was purified by column chromatography (silica gel, 20% ethyl acetate in hexane) to afford the title compound. LCMS: 168.3 (M+H)+. the organic layer was separated washed with water and brine After drying over sodium sulfate, filtration, and concentration the residue was purified by column chromatography (silica gel, 20% ethyl acetate in hexane)

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

Procedure: To a solution of Example 10A (500 mg, 4.58 mmol) in dichloromethane (10 mL) was added triethylamine (2.55 mL, 18.32 mmol) followed by propane-2-sulfonyl chloride (1.306 g, 9.16 mmol) and the mixture was stirred for 3 hours. The mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by column chromatography (silica gel, 30% ethyl acetate in hexane) afforded the title compound. LCMS: 216.2 (M+H-Boc)+. The mixture was concentrated the residue was dissolved in ethyl acetate washed with water and brine dried over anhydrous sodium sulfate filtered concentrated Purification by column chromatography (silica gel, 30% ethyl acetate in hexane)