9H-fluoren-9-ylmethyl N-prop-2-ynylcarbamate

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

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

Procedure: A solution of Fmoc chloride (25.00 g, 96.64 mmol, 1.05 eq.) in DCM (150 mL) was added dropwise to a solution of propargylamine 8 (5.89 mL, 92.04 mmol, 1.0 eq.) and triethylamine (15.4 mL, 110.4 mmol, 1.2 eq.) in DCM (200 mL) at −78° C. The reaction mixture was allowed to stir at room temperature, and after 16 hours the solution was washed with water (300 mL), 0.1 N aqueous citric acid (300 mL), saturated aqueous NaHCO3 (300 mL) and brine (200 mL). The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide an amorphous white powder. Sonication in cold hexane (200 mL) followed by filtration afforded the product as a white solid (24.316 g, 95%). LC/MS (2.758 min (ES+)). m/z: 300.0 [M+Na]+. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, 2H, J=7.6 Hz), 7.57 (d, 2H, J=7.4 Hz), 7.41-7.37 (m, 2H), 7.30 (dt, 2H, J=7.5, 1.2 Hz), 4.93 (br s, 1H), 4.41 (d, 2H, J=6.9 Hz), 4.21 (t, 1H, J=6.4 Hz), 3.99 (d, 2H, J=3.3 Hz), 2.24 (t, 1H, J=2.5 Hz). after 16 hours the solution was washed with water (300 mL), 0.1 N aqueous citric acid (300 mL), saturated aqueous NaHCO3 (300 mL) and brine (200 mL) The organic phase was dried over magnesium sulphate filtered concentrated under reduced pressure to provide an amorphous white powder followed by filtration

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 propargylamine (250 μL, 3.645 mmol) in diisopropylethylamine (1.273 mL, 7.290 mmol), was added 9-fluorenylmethyl chloroformate (Fmoc), dissolved in 7 mL dimethylformamide. The mixture was stirred under argon overnight at room temperature. After completion, the solution was reduced in vacuo. An ethyl acetate/water extraction procedure was performed to isolate the product; MS: 278.10 (m/z). An ethyl acetate/water extraction procedure to isolate the product

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

Procedure: A solution of Fmoc chloride (25.00 g, 96.64 mmol, 1.05 eq.) in DCM (150 mL) was added dropwise to a solution of propargylamine 8 (5.89 mL, 92.04 mmol, 1.0 eq.) and triethylamine (15.4 mL, 110.4 mmol, 1.2 eq.) in DCM (200 mL) at −78° C. The reaction mixture was allowed to stir at room temperature, and after 16 hours the solution was washed with water (300 mL), 0.1 N aqueous citric acid (300 mL), saturated aqueous NaHCO3 (300 mL) and brine (200 mL). The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide an amorphous white powder. Sonication in cold hexane (200 mL) followed by filtration afforded the product as a white solid (24.316 g, 95%). LC/MS (2.758 min (ES+)). m/z: 300.0 [M+Na]+. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, 2H, J=7.6 Hz), 7.57 (d, 2H, J=7.4 Hz), 7.41-7.37 (m, 2H), 7.30 (dt, 2H, J=7.5, 1.2 Hz), 4.93 (br s, 1H), 4.41 (d, 2H, J=6.9 Hz), 4.21 (t, 1H, J=6.4 Hz), 3.99 (d, 2H, J=3.3 Hz), 2.24 (t, 1H, J=2.5 Hz). after 16 hours the solution was washed with water (300 mL), 0.1 N aqueous citric acid (300 mL), saturated aqueous NaHCO3 (300 mL) and brine (200 mL) The organic phase was dried over magnesium sulphate filtered concentrated under reduced pressure to provide an amorphous white powder followed by filtration