Ethyl 4-(Dibenzylamino)butanoate

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

Procedure: To a solution of 500 mg (1.6 mmol, 1 equiv.) of 4-dibenzylamino-butyric acid ethyl ester in 1 ml of THF was added 4 ml of HCl 2N and the resulting mixture was stirred for 48 hours. After decantation and separation, the aqueous layer was extracted twice by ethyl acetate. The pH was fixed to 5 using solid sodium carbonate and the aqueous layer was extracted by dichloromethane. The dichloromethane layer was dried over sodium sulphate, evaporated and used without further purification. After decantation and separation the aqueous layer was extracted twice by ethyl acetate the aqueous layer was extracted by dichloromethane The dichloromethane layer was dried over sodium sulphate evaporated used without further purification

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

Procedure: To a solution of 500 mg (1.6 mmol, 1 equiv.) of 4-dibenzylamino-butyric acid ethyl ester in 1 ml of THF was added 4 ml of HCl 2N and the resulting mixture was stirred for 48 hours. After decantation and separation, the aqueous layer was extracted twice by ethyl acetate. The pH was fixed to 5 using solid sodium carbonate and the aqueous layer was extracted by dichloromethane. The dichloromethane layer was dried over sodium sulphate, evaporated and used without further purification. After decantation and separation the aqueous layer was extracted twice by ethyl acetate the aqueous layer was extracted by dichloromethane The dichloromethane layer was dried over sodium sulphate evaporated used without further purification

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

Procedure: Mix ethyl 4-iodobutyrate (43.5 g, 0.18 mol), dibenzylamine (35.5 g, 0.18 mol), potassium carbonate (24.9 g, 0.18 mol) and ethanol (114 mL dried over 4A molecular sieves). Reflux for 24 hours then stir at room temperature for 48 hours. Add methylene chloride (100 mL) and filter. Evaporate the filtrate to a residue and purify by silica gel chromatography (methylene chloride) to give the title compound (47 g). Reflux for 24 hours Add methylene chloride (100 mL) and filter Evaporate the filtrate to a residue purify by silica gel chromatography (methylene chloride)

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

Procedure: In step b, the 4-iodo functionality of the appropriate ethyl 4-iodobutyrate of structure (52) is displaced with dibenzylamine to give the corresponding 4-dibenzylaminobutyric acid, ethyl ester of structure (53).

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

Procedure: Mix ethyl 4-iodobutyrate (43.5 g, 0.18 mol), dibenzylamine (35.5 g, 0.18 mol), potassium carbonate (24.9 g, 0.18 mol) and ethanol (114 mL dried over 4A molecular sieves). Reflux for 24 hours then stir at room temperature for 48 hours. Add methylene chloride (100 mL) and filter. Evaporate the filtrate to a residue and purify by silica gel chromatography (methylene chloride) to give the title compound (47 g). Reflux for 24 hours Add methylene chloride (100 mL) and filter Evaporate the filtrate to a residue purify by silica gel chromatography (methylene chloride)

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

Procedure: In step b, the 4-iodo functionality of the appropriate ethyl 4-iodobutyrate of structure (52) is displaced with dibenzylamine to give the corresponding 4-dibenzylaminobutyric acid, ethyl ester of structure (53).

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

Procedure: Mix ethyl 4-iodobutyrate (43.5 g, 0.18 mol), dibenzylamine (35.5 g, 0.18 mol), potassium carbonate (24.9 g, 0.18 mol) and ethanol (114 mL dried over 4A molecular sieves). Reflux for 24 hours then stir at room temperature for 48 hours. Add methylene chloride (100 mL) and filter. Evaporate the filtrate to a residue and purify by silica gel chromatography (methylene chloride) to give the title compound (47 g). Reflux for 24 hours Add methylene chloride (100 mL) and filter Evaporate the filtrate to a residue purify by silica gel chromatography (methylene chloride)

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

Procedure: In step b, the 4-iodo functionality of the appropriate ethyl 4-iodobutyrate of structure (52) is displaced with dibenzylamine to give the corresponding 4-dibenzylaminobutyric acid, ethyl ester of structure (53).

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of ethyl 4-bromobutyrate (2.0 g, 10.25 mmol), dibenzylamine (2.02 g, 10.25 mmol) and potassium carbonate (2.83 g, 20.5 mmol) in N,N-dimethylformamide (20 mL) was heated with stirring at 100° C. overnight. The resulting mixture was diluted with water (80 mL) and then extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine (80 mL×2), and then dried over Na2SO4 and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc:PE=1:4) to afford ethyl 4-(dibenzylamino)butanoate as a white solid (2.0 g, yield: 64%). was heated extracted with ethyl acetate (50 mL×3) The combined organic layers were washed with brine (80 mL×2) dried over Na2SO4 concentrated in vacuo The residue was purified by flash chromatography on silica gel (EtOAc:PE=1:4)

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

Procedure: To a solution of 500 mg (1.6 mmol, 1 equiv.) of 4-dibenzylamino-butyric acid ethyl ester in 1 ml of THF was added 4 ml of HCl 2N and the resulting mixture was stirred for 48 hours. After decantation and separation, the aqueous layer was extracted twice by ethyl acetate. The pH was fixed to 5 using solid sodium carbonate and the aqueous layer was extracted by dichloromethane. The dichloromethane layer was dried over sodium sulphate, evaporated and used without further purification. After decantation and separation the aqueous layer was extracted twice by ethyl acetate the aqueous layer was extracted by dichloromethane The dichloromethane layer was dried over sodium sulphate evaporated used without further purification

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

Procedure: Mix ethyl 4-iodobutyrate (43.5 g, 0.18 mol), dibenzylamine (35.5 g, 0.18 mol), potassium carbonate (24.9 g, 0.18 mol) and ethanol (114 mL dried over 4A molecular sieves). Reflux for 24 hours then stir at room temperature for 48 hours. Add methylene chloride (100 mL) and filter. Evaporate the filtrate to a residue and purify by silica gel chromatography (methylene chloride) to give the title compound (47 g). Reflux for 24 hours Add methylene chloride (100 mL) and filter Evaporate the filtrate to a residue purify by silica gel chromatography (methylene chloride)

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

Procedure: In step b, the 4-iodo functionality of the appropriate ethyl 4-iodobutyrate of structure (52) is displaced with dibenzylamine to give the corresponding 4-dibenzylaminobutyric acid, ethyl ester of structure (53).