tert-butyl N-(3-methylbutyl)carbamate

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

Procedure: To a stirred solution of tert-butyl iso-pentylcarbamate (1.87 g, 9.99 mmol, 1.00 equiv) in tetrahydrofuran (10 mL) at 0° C. was added sodium hydride (600 mg, 25.00 mmol, 1.20 equiv). When the evolution of hydrogen subsided, iodoethane (1.7 g, 10.90 mmol, 1.10 equiv) was then added dropwise to the reaction mixture. The resulting solution was stirred at room temperature for 15 h. It was then diluted with 50 mL of dichloromethane and washed with 4×20 mL of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether to give 0.51 g (24%) of tert-butyl ethyl(iso-pentyl)carbamate as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ 3.25-3.14 (m, 4H), 1.57-1.46 (m, 1H), 1.46 (s, 9H), 1.40-1.36 (m, 2H), 1.09 (t, J=7.2 Hz, 3H), 0.92 (d, J=8.8 Hz, 6H) ppm. LCMS (method D, ESI): RT=1.81 min, m/z=216.0 [M+H]+. washed with 4×20 mL of brine The organic layer was dried over sodium sulfate concentrated under vacuum The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether

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

Procedure: To a stirred solution of tert-butyl iso-pentylcarbamate (1.87 g, 9.99 mmol, 1.00 equiv) in tetrahydrofuran (10 mL) at 0° C. was added sodium hydride (600 mg, 25.00 mmol, 1.20 equiv). When the evolution of hydrogen subsided, iodoethane (1.7 g, 10.90 mmol, 1.10 equiv) was then added dropwise to the reaction mixture. The resulting solution was stirred at room temperature for 15 h. It was then diluted with 50 mL of dichloromethane and washed with 4×20 mL of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether to give 0.51 g (24%) of tert-butyl ethyl(iso-pentyl)carbamate as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ 3.25-3.14 (m, 4H), 1.57-1.46 (m, 1H), 1.46 (s, 9H), 1.40-1.36 (m, 2H), 1.09 (t, J=7.2 Hz, 3H), 0.92 (d, J=8.8 Hz, 6H) ppm. LCMS (method D, ESI): RT=1.81 min, m/z=216.0 [M+H]+. washed with 4×20 mL of brine The organic layer was dried over sodium sulfate concentrated under vacuum The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether

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

Procedure: To a stirred solution of tert-butyl iso-pentylcarbamate (1.87 g, 9.99 mmol, 1.00 equiv) in tetrahydrofuran (10 mL) at 0° C. was added sodium hydride (600 mg, 25.00 mmol, 1.20 equiv). When the evolution of hydrogen subsided, iodoethane (1.7 g, 10.90 mmol, 1.10 equiv) was then added dropwise to the reaction mixture. The resulting solution was stirred at room temperature for 15 h. It was then diluted with 50 mL of dichloromethane and washed with 4×20 mL of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether to give 0.51 g (24%) of tert-butyl ethyl(iso-pentyl)carbamate as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ 3.25-3.14 (m, 4H), 1.57-1.46 (m, 1H), 1.46 (s, 9H), 1.40-1.36 (m, 2H), 1.09 (t, J=7.2 Hz, 3H), 0.92 (d, J=8.8 Hz, 6H) ppm. LCMS (method D, ESI): RT=1.81 min, m/z=216.0 [M+H]+. washed with 4×20 mL of brine The organic layer was dried over sodium sulfate concentrated under vacuum The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether

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

Procedure: To a stirred solution of tert-butyl iso-pentylcarbamate (1.87 g, 9.99 mmol, 1.00 equiv) in tetrahydrofuran (10 mL) at 0° C. was added sodium hydride (600 mg, 25.00 mmol, 1.20 equiv). When the evolution of hydrogen subsided, iodoethane (1.7 g, 10.90 mmol, 1.10 equiv) was then added dropwise to the reaction mixture. The resulting solution was stirred at room temperature for 15 h. It was then diluted with 50 mL of dichloromethane and washed with 4×20 mL of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether to give 0.51 g (24%) of tert-butyl ethyl(iso-pentyl)carbamate as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ 3.25-3.14 (m, 4H), 1.57-1.46 (m, 1H), 1.46 (s, 9H), 1.40-1.36 (m, 2H), 1.09 (t, J=7.2 Hz, 3H), 0.92 (d, J=8.8 Hz, 6H) ppm. LCMS (method D, ESI): RT=1.81 min, m/z=216.0 [M+H]+. washed with 4×20 mL of brine The organic layer was dried over sodium sulfate concentrated under vacuum The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether