2-(dimethylamino)propanoic acid;hydrochloride

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

Procedure: Dry methylene chloride (30 ml) and triethylamine (0.33 ml, 2.34 mmole) are added to a mixture of 2,3-diethyl-4-methoxynaphthol (180 mg, 0.78 mmole), dimethylamino propionic acid hydrochloride (2 eq, 283 mg, 1.56 mmole), dicyclohexylcarbodiimide (2 eq, 322 mg, 1.56 mmole) and 4-dimethylaminpyridine (1 eq, 95 mg, 0.78 mmole) at room temperature under argon, and the resulting suspension is stirred at room temperature under argon for two days. The white precipitate is removed by filtration, and the filtrate is concentrated. Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane isolates 144 mg (51.8% ) of 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a colorless oil. The white precipitate is removed by filtration the filtrate is concentrated Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane

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

Procedure: Dry methylene chloride (30 ml) and triethylamine (0.33 ml, 2.34 mmole) are added to a mixture of 2,3-diethyl-4-methoxynaphthol (180 mg, 0.78 mmole), dimethylamino propionic acid hydrochloride (2 eq, 283 mg, 1.56 mmole), dicyclohexylcarbodiimide (2 eq, 322 mg, 1.56 mmole) and 4-dimethylaminpyridine (1 eq, 95 mg, 0.78 mmole) at room temperature under argon, and the resulting suspension is stirred at room temperature under argon for two days. The white precipitate is removed by filtration, and the filtrate is concentrated. Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane isolates 144 mg (51.8% ) of 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a colorless oil. The white precipitate is removed by filtration the filtrate is concentrated Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane

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

Procedure: After adding N,N-dimethylaminopropionic acid hydrochloride (1.46 g), triethylamine (1.45 ml), 1-hydroxybenzotriazole (1.93 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.19 g) to a solution of 4-(tert-butoxycarbonylamino)piperidine (1.9 g) in N,N-dimethylformamide (30 ml), the mixture was stirred for 27.5 hours at room temperature under a nitrogen atmosphere. Ethyl acetate (200 ml), brine (50 ml) and 1N aqueous sodium hydroxide (50 ml) were added to the reaction mixture and stirred therewith at room temperature for 30 minutes, and then the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and then washed with 1N aqueous sodium hydroxide and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to provide the title compound (2.96 g, quantitative) as pale yellow crystals. stirred at room temperature for 30 minutes the mixture was partitioned The aqueous layer was extracted with ethyl acetate washed with 1N aqueous sodium hydroxide and brine dried over anhydrous sodium sulfate The dried organic layer was concentrated under reduced pressure

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

Procedure: After adding N,N-dimethylaminopropionic acid hydrochloride (1.46 g), triethylamine (1.45 ml), 1-hydroxybenzotriazole (1.93 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.19 g) to a solution of 4-(tert-butoxycarbonylamino)piperidine (1.9 g) in N,N-dimethylformamide (30 ml), the mixture was stirred for 27.5 hours at room temperature under a nitrogen atmosphere. Ethyl acetate (200 ml), brine (50 ml) and 1N aqueous sodium hydroxide (50 ml) were added to the reaction mixture and stirred therewith at room temperature for 30 minutes, and then the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and then washed with 1N aqueous sodium hydroxide and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to provide the title compound (2.96 g, quantitative) as pale yellow crystals. stirred at room temperature for 30 minutes the mixture was partitioned The aqueous layer was extracted with ethyl acetate washed with 1N aqueous sodium hydroxide and brine dried over anhydrous sodium sulfate The dried organic layer was concentrated under reduced pressure

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

Procedure: Dry methylene chloride (30 ml) and triethylamine (0.33 ml, 2.34 mmole) are added to a mixture of 2,3-diethyl-4-methoxynaphthol (180 mg, 0.78 mmole), dimethylamino propionic acid hydrochloride (2 eq, 283 mg, 1.56 mmole), dicyclohexylcarbodiimide (2 eq, 322 mg, 1.56 mmole) and 4-dimethylaminpyridine (1 eq, 95 mg, 0.78 mmole) at room temperature under argon, and the resulting suspension is stirred at room temperature under argon for two days. The white precipitate is removed by filtration, and the filtrate is concentrated. Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane isolates 144 mg (51.8% ) of 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a colorless oil. The white precipitate is removed by filtration the filtrate is concentrated Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane

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

Procedure: After adding N,N-dimethylaminopropionic acid hydrochloride (1.46 g), triethylamine (1.45 ml), 1-hydroxybenzotriazole (1.93 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.19 g) to a solution of 4-(tert-butoxycarbonylamino)piperidine (1.9 g) in N,N-dimethylformamide (30 ml), the mixture was stirred for 27.5 hours at room temperature under a nitrogen atmosphere. Ethyl acetate (200 ml), brine (50 ml) and 1N aqueous sodium hydroxide (50 ml) were added to the reaction mixture and stirred therewith at room temperature for 30 minutes, and then the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and then washed with 1N aqueous sodium hydroxide and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to provide the title compound (2.96 g, quantitative) as pale yellow crystals. stirred at room temperature for 30 minutes the mixture was partitioned The aqueous layer was extracted with ethyl acetate washed with 1N aqueous sodium hydroxide and brine dried over anhydrous sodium sulfate The dried organic layer was concentrated under reduced pressure