N-(2-phenylethyl)but-3-en-1-amine

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 1 (12.6 g, 49.75 mmol) in THF (200 mL) is added KOTMS (6.38 g, 49.75 mmol). The mixture is stirred overnight at room temperature. The mixture is concentrated and the residue dissolved in dichloromethane (200 mL) and cooled to 0° C. Trimethylacetyl chloride (5.94 g, 49.25 mmol) is added slowly and the mixture is warmed to room temperature over 2 hours. The mixture is cooled to −78° C., 2 (8.63 g, 49.25 mmol) is added and stirring continued at −78° C. for 1.5 h. Saturated sodium bicarbonate (100 mL) is added and the mixture is allowed to warm to rt. The mixture is extracted with EtOAc (4×100 mL) and the organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 15 g (76%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=399.37. The mixture is concentrated the residue dissolved in dichloromethane (200 mL) cooled to 0° C the mixture is warmed to room temperature over 2 hours The mixture is cooled to −78° C. stirring continued at −78° C. for 1.5 h to warm to rt The mixture is extracted with EtOAc (4×100 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 2-phenylethylamine (72 mL, 570 mmol) is added K2CO3 (82 g, 570 mmol) and 4-bromo-1-butene (25 g, 185 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added. The mixture is extracted with EtOAc (4×150 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 20 g (62%) of the title compound. M+H+=176.10. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added The mixture is extracted with EtOAc (4×150 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 1 (12.6 g, 49.75 mmol) in THF (200 mL) is added KOTMS (6.38 g, 49.75 mmol). The mixture is stirred overnight at room temperature. The mixture is concentrated and the residue dissolved in dichloromethane (200 mL) and cooled to 0° C. Trimethylacetyl chloride (5.94 g, 49.25 mmol) is added slowly and the mixture is warmed to room temperature over 2 hours. The mixture is cooled to −78° C., 2 (8.63 g, 49.25 mmol) is added and stirring continued at −78° C. for 1.5 h. Saturated sodium bicarbonate (100 mL) is added and the mixture is allowed to warm to rt. The mixture is extracted with EtOAc (4×100 mL) and the organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 15 g (76%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=399.37. The mixture is concentrated the residue dissolved in dichloromethane (200 mL) cooled to 0° C the mixture is warmed to room temperature over 2 hours The mixture is cooled to −78° C. stirring continued at −78° C. for 1.5 h to warm to rt The mixture is extracted with EtOAc (4×100 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 2-phenylethylamine (72 mL, 570 mmol) is added K2CO3 (82 g, 570 mmol) and 4-bromo-1-butene (25 g, 185 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added. The mixture is extracted with EtOAc (4×150 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 20 g (62%) of the title compound. M+H+=176.10. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added The mixture is extracted with EtOAc (4×150 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 1 (12.6 g, 49.75 mmol) in THF (200 mL) is added KOTMS (6.38 g, 49.75 mmol). The mixture is stirred overnight at room temperature. The mixture is concentrated and the residue dissolved in dichloromethane (200 mL) and cooled to 0° C. Trimethylacetyl chloride (5.94 g, 49.25 mmol) is added slowly and the mixture is warmed to room temperature over 2 hours. The mixture is cooled to −78° C., 2 (8.63 g, 49.25 mmol) is added and stirring continued at −78° C. for 1.5 h. Saturated sodium bicarbonate (100 mL) is added and the mixture is allowed to warm to rt. The mixture is extracted with EtOAc (4×100 mL) and the organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 15 g (76%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=399.37. The mixture is concentrated the residue dissolved in dichloromethane (200 mL) cooled to 0° C the mixture is warmed to room temperature over 2 hours The mixture is cooled to −78° C. stirring continued at −78° C. for 1.5 h to warm to rt The mixture is extracted with EtOAc (4×100 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 2-phenylethylamine (72 mL, 570 mmol) is added K2CO3 (82 g, 570 mmol) and 4-bromo-1-butene (25 g, 185 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added. The mixture is extracted with EtOAc (4×150 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 20 g (62%) of the title compound. M+H+=176.10. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added The mixture is extracted with EtOAc (4×150 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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 1 (12.6 g, 49.75 mmol) in THF (200 mL) is added KOTMS (6.38 g, 49.75 mmol). The mixture is stirred overnight at room temperature. The mixture is concentrated and the residue dissolved in dichloromethane (200 mL) and cooled to 0° C. Trimethylacetyl chloride (5.94 g, 49.25 mmol) is added slowly and the mixture is warmed to room temperature over 2 hours. The mixture is cooled to −78° C., 2 (8.63 g, 49.25 mmol) is added and stirring continued at −78° C. for 1.5 h. Saturated sodium bicarbonate (100 mL) is added and the mixture is allowed to warm to rt. The mixture is extracted with EtOAc (4×100 mL) and the organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 15 g (76%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=399.37. The mixture is concentrated the residue dissolved in dichloromethane (200 mL) cooled to 0° C the mixture is warmed to room temperature over 2 hours The mixture is cooled to −78° C. stirring continued at −78° C. for 1.5 h to warm to rt The mixture is extracted with EtOAc (4×100 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 2-phenylethylamine (72 mL, 570 mmol) is added K2CO3 (82 g, 570 mmol) and 4-bromo-1-butene (25 g, 185 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added. The mixture is extracted with EtOAc (4×150 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 20 g (62%) of the title compound. M+H+=176.10. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added The mixture is extracted with EtOAc (4×150 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 1 (12.6 g, 49.75 mmol) in THF (200 mL) is added KOTMS (6.38 g, 49.75 mmol). The mixture is stirred overnight at room temperature. The mixture is concentrated and the residue dissolved in dichloromethane (200 mL) and cooled to 0° C. Trimethylacetyl chloride (5.94 g, 49.25 mmol) is added slowly and the mixture is warmed to room temperature over 2 hours. The mixture is cooled to −78° C., 2 (8.63 g, 49.25 mmol) is added and stirring continued at −78° C. for 1.5 h. Saturated sodium bicarbonate (100 mL) is added and the mixture is allowed to warm to rt. The mixture is extracted with EtOAc (4×100 mL) and the organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 15 g (76%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=399.37. The mixture is concentrated the residue dissolved in dichloromethane (200 mL) cooled to 0° C the mixture is warmed to room temperature over 2 hours The mixture is cooled to −78° C. stirring continued at −78° C. for 1.5 h to warm to rt The mixture is extracted with EtOAc (4×100 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

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

Procedure: To a solution of 2-phenylethylamine (72 mL, 570 mmol) is added K2CO3 (82 g, 570 mmol) and 4-bromo-1-butene (25 g, 185 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added. The mixture is extracted with EtOAc (4×150 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 20 g (62%) of the title compound. M+H+=176.10. The solution is evaporated to dryness and H2O/EtOAc (1:1) (600 mL) is added The mixture is extracted with EtOAc (4×150 mL) dried concentrated under vacuum The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)