Methyl 3-(tert-butoxycarbonylaMino)propanoate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve diisopropylamine (5.6 mL, 40 mmol) in anhydrous tetrahydrofuran, cool to -78° C. and place under nitrogen atmosphere. Treat with n-butyllithium (25 mL of a 1.6M solution in hexane, 40 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-β-alanine methyl ester (4.06 g, 20 mmol) in tetrahydrofuran (25 mL) over 20 minutes. Stir for an additional 30 minutes. Add allyl bromide (1.72 mL, 20 mmol) and allow the mixture to warm to room temperature with stirring until homogeneous. Cool to -78° C. and slowly warm to -20° C. over 30 minutes. Pour into 5% hydrochloric acid, extract into ether, wash with saturated sodium chloride, dry, and concentrate to yield 5.01 g yellow oil. Purify by silica gel chromatography (25% ethyl acetate/hexane) to yield 4.2 g (87%) of a racemic mixture of the title compound as a clear colorless oil. add, by dropwise addition Stir for an additional 30 minutes to warm to room temperature with stirring until homogeneous Cool to -78° C. slowly warm to -20° C. over 30 minutes extract into ether wash with saturated sodium chloride dry concentrate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve diisopropylamine (5.6 mL, 40 mmol) in anhydrous tetrahydrofuran, cool to -78° C. and place under nitrogen atmosphere. Treat with n-butyllithium (25 mL of a 1.6M solution in hexane, 40 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-β-alanine methyl ester (4.06 g, 20 mmol) in tetrahydrofuran (25 mL) over 20 minutes. Stir for an additional 30 minutes. Add allyl bromide (1.72 mL, 20 mmol) and allow the mixture to warm to room temperature with stirring until homogeneous. Cool to -78° C. and slowly warm to -20° C. over 30 minutes. Pour into 5% hydrochloric acid, extract into ether, wash with saturated sodium chloride, dry, and concentrate to yield 5.01 g yellow oil. Purify by silica gel chromatography (25% ethyl acetate/hexane) to yield 4.2 g (87%) of a racemic mixture of the title compound as a clear colorless oil. add, by dropwise addition Stir for an additional 30 minutes to warm to room temperature with stirring until homogeneous Cool to -78° C. slowly warm to -20° C. over 30 minutes extract into ether wash with saturated sodium chloride dry concentrate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve diisopropylamine (5.6 mL, 40 mmol) in anhydrous tetrahydrofuran, cool to -78° C. and place under nitrogen atmosphere. Treat with n-butyllithium (25 mL of a 1.6M solution in hexane, 40 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-β-alanine methyl ester (4.06 g, 20 mmol) in tetrahydrofuran (25 mL) over 20 minutes. Stir for an additional 30 minutes. Add allyl bromide (1.72 mL, 20 mmol) and allow the mixture to warm to room temperature with stirring until homogeneous. Cool to -78° C. and slowly warm to -20° C. over 30 minutes. Pour into 5% hydrochloric acid, extract into ether, wash with saturated sodium chloride, dry, and concentrate to yield 5.01 g yellow oil. Purify by silica gel chromatography (25% ethyl acetate/hexane) to yield 4.2 g (87%) of a racemic mixture of the title compound as a clear colorless oil. add, by dropwise addition Stir for an additional 30 minutes to warm to room temperature with stirring until homogeneous Cool to -78° C. slowly warm to -20° C. over 30 minutes extract into ether wash with saturated sodium chloride dry concentrate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve diisopropylamine (5.6 mL, 40 mmol) in anhydrous tetrahydrofuran, cool to -78° C. and place under nitrogen atmosphere. Treat with n-butyllithium (25 mL of a 1.6M solution in hexane, 40 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-β-alanine methyl ester (4.06 g, 20 mmol) in tetrahydrofuran (25 mL) over 20 minutes. Stir for an additional 30 minutes. Add allyl bromide (1.72 mL, 20 mmol) and allow the mixture to warm to room temperature with stirring until homogeneous. Cool to -78° C. and slowly warm to -20° C. over 30 minutes. Pour into 5% hydrochloric acid, extract into ether, wash with saturated sodium chloride, dry, and concentrate to yield 5.01 g yellow oil. Purify by silica gel chromatography (25% ethyl acetate/hexane) to yield 4.2 g (87%) of a racemic mixture of the title compound as a clear colorless oil. add, by dropwise addition Stir for an additional 30 minutes to warm to room temperature with stirring until homogeneous Cool to -78° C. slowly warm to -20° C. over 30 minutes extract into ether wash with saturated sodium chloride dry concentrate

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.20 g (21.54 mmol) N-hydroxy-isobutyramidine are placed in 10 ml dimethylformamide and molecular sieve. 0.948 g (23.69 mmol) sodium hydride (60% in mineral oil) are added. The mixture is stirred for 0.1 hours at 50° C., then 6.20 g (30.51 mmol) methyl 3-tert-butoxycarbonylamino-propionate in 20 ml dimethylformamide are added. The reaction mixture is stirred for 3 hours at 50° C. After cooling 15 ml of water are added, the mixture is suction filtered through Celite. The 2 phases of the filtrate are separated, the aqueous phase is extracted with ethyl acetate, the combined organic phase is evaporated down. The residue is purified by chromatography. The reaction mixture is stirred for 3 hours at 50° C are added filtered through Celite The 2 phases of the filtrate are separated the aqueous phase is extracted with ethyl acetate the combined organic phase is evaporated down The residue is purified by chromatography

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.20 g (21.54 mmol) N-hydroxy-isobutyramidine are placed in 10 ml dimethylformamide and molecular sieve. 0.948 g (23.69 mmol) sodium hydride (60% in mineral oil) are added. The mixture is stirred for 0.1 hours at 50° C., then 6.20 g (30.51 mmol) methyl 3-tert-butoxycarbonylamino-propionate in 20 ml dimethylformamide are added. The reaction mixture is stirred for 3 hours at 50° C. After cooling 15 ml of water are added and the mixture is suction filtered through Celite. The 2 phases of the filtrate are separated, the aqueous phase is extracted with ethyl acetate, the combined organic phases are evaporated down. The residue is purified by chromatography. The reaction mixture is stirred for 3 hours at 50° C are added filtered through Celite The 2 phases of the filtrate are separated the aqueous phase is extracted with ethyl acetate the combined organic phases are evaporated down The residue is purified by chromatography

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.00 g (22.70 mmol) N-hydroxy-propionamidine are placed in 10 ml dimethylformamide and molecular sieve. 0.999 g (24.97 mmol) sodium hydride (60% in mineral oil) are added. The mixture is stirred for 0.1 hours at 50° C., then 5.00 g (24.60 mmol) methyl3-tert-butoxycarbonylamino-propionate in 20 ml dimethylformamide are added. The reaction mixture is stirred for 3 hours at 50° C. After cooling 15 ml of water are added, and the mixture is suction filtered through Celite. The 2 phases of the filtrate are separated and the organic phase is evaporated down. The residue is purified by chromatography. The reaction mixture is stirred for 3 hours at 50° C are added filtered through Celite The 2 phases of the filtrate are separated the organic phase is evaporated down The residue is purified by chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve diisopropylamine (5.6mL, 40mmol) in anhydrous tetrahydrofuran, cool to -78° C. and place under nitrogen atmosphere. Treat with n-butyllithium (25mL of a 1.6M solution in hexane, 40mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-β-alanine methyl ester (4.06g, 20mmol) in tetrahydrofuran (25mL) over 20 minutes. Stir for an additional 30 minutes. Add allyl bromide (1.72mL, 20mmol) and allow the mixture to warm to room temperature with stirring until homogeneous. Cool to -78° C. and slowly warm to -20° C. over 30 minutes. Pour into 5% hydrochloric acid, extract into ether, wash with saturated sodium chloride, dry, and concentrate to yield 5.01g yellow oil. Purify by silica gel chromatography (25% ethyl acetate/hexane) to yield 4.2g (87%) of a racemic mixture of the title compound as a clear colorless oil. add, by dropwise addition Stir for an additional 30 minutes to warm to room temperature with stirring until homogeneous Cool to -78° C. slowly warm to -20° C. over 30 minutes extract into ether wash with saturated sodium chloride dry concentrate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve diisopropylamine (5.6 mL, 40 mmol) in anhydrous tetrahydrofuran, cool to -78° C. and place under nitrogen atmosphere. Treat with n-butyllithium (25 mL of a 1.6M solution in hexane, 40 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(t-butyloxycarbonyl)-β-alanine methyl ester (4.06 g, 20 mmol) in tetrahydrofuran (25 mL) over 20 minutes. Stir for an additional 30 minutes. Add allyl bromide (1.72 mL, 20 mmol) and allow the mixture to warm to room temperature with stirring until homogeneous. Cool to -78° C. and slowly warm to -20° C. over 30 minutes. Pour into 5% hydrochloric acid, extract into ether, wash with saturated sodium chloride, dry, and concentrate to yield 5.01 g yellow oil. Purify by silica gel chromatography (25% ethyl acetate/hexane) to yield 4.2 g (87%) of a racemic mixture of the title compound as a clear colorless oil. add, by dropwise addition Stir for an additional 30 minutes to warm to room temperature with stirring until homogeneous Cool to -78° C. slowly warm to -20° C. over 30 minutes extract into ether wash with saturated sodium chloride dry concentrate