ethyl 3-(benzylamino)butanoate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a suspension of lithium aluminum hydride (0.76 g, 20 mmol) in cyclopentylmethylether (20 mL) was added a solution of 3-benzylamino-butyric acid ethyl ester (2.10 g, 9.5 mmol) in cyclopentylmethylether (10 mL) dropwise at 0° C. under nitrogen atmosphere. The resulting mixture was warmed to room temperature and stirred for 3 hours. Then small amount of sodium sulfate saturated aqueous solution was added dropwise to quench the reaction at 0° C. and stirred for one hour. The resulting solid material was removed by filtration and the organic solution was concentrated to yield 3-benzylamino-butan-1-ol (1.49 g, 8.3 mmol, 87%) as colorless oil. The oil was used in the subsequent step without further purification. to quench the reaction at 0° C. stirred for one hour The resulting solid material was removed by filtration the organic solution was concentrated

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

Procedure: To a suspension of lithium aluminum hydride (0.76 g, 20 mmol) in cyclopentylmethylether (20 mL) was added a solution of 3-benzylamino-butyric acid ethyl ester (2.10 g, 9.5 mmol) in cyclopentylmethylether (10 mL) dropwise at 0° C. under nitrogen atmosphere. The resulting mixture was warmed to room temperature and stirred for 3 hours. Then small amount of sodium sulfate saturated aqueous solution was added dropwise to quench the reaction at 0° C. and stirred for one hour. The resulting solid material was removed by filtration and the organic solution was concentrated to yield 3-benzylamino-butan-1-ol (1.49 g, 8.3 mmol, 87%) as colorless oil. The oil was used in the subsequent step without further purification. to quench the reaction at 0° C. stirred for one hour The resulting solid material was removed by filtration the organic solution was concentrated

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

Procedure: To a solution of 3-amino-butyric acid ethyl ester (5.00 g, 34.3 mmol), benzaldehyde (4.1 mL, 40 mmol) and acetic acid (1.9 mL, 34 mmol) in 1,2-dichloroethane (120 mL) was added sodium triacetoxyborohydride (17 g, 80 mmol) at room temperature and the mixture was stirred for 20 hours. The reaction mixture was poured into sodium bicarbonate saturated aqueous solution and extracted with chloroform. The organic phase was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant) to afford 3-benzylamino-butyric acid ethyl ester (2.1 g, 9.5 mmol, 28%) as colorless oil. extracted with chloroform The organic phase was dried over anhydrous sodium sulfate concentrated The resulting residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A suspension of ethyl 3-(benzylamino)butanoate (5.9 g, 26.7 mmol), methyl bromoacetate (3.0 ml, 31.7 mmol) and potassium carbonate (7.4 g, 53.5 mmol) in acetonitrile (100 ml), was stirred at room temperature for 18 hs. The reaction was filtered through celite and concentrated to give ethyl 3-[benzyl(2-methoxy-2-oxoethyl)amino]butanoate (6.45 g, 82%) as a clear oil, MS (M+H)+=294. The reaction was filtered through celite and concentrated

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

Procedure: A suspension of ethyl 3-(benzylamino)butanoate (5.9 g, 26.7 mmol), methyl bromoacetate (3.0 ml, 31.7 mmol) and potassium carbonate (7.4 g, 53.5 mmol) in acetonitrile (100 ml), was stirred at room temperature for 18 hs. The reaction was filtered through celite and concentrated to give ethyl 3-[benzyl(2-methoxy-2-oxoethyl)amino]butanoate (6.45 g, 82%) as a clear oil, MS (M+H)+=294. The reaction was filtered through celite and concentrated

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

Procedure: A solution of ethyl crotonate (5.0 ml, 40 mmol) and benzyl amine (4.8 ml, 44 mmol) was heated to 100° C. for 18 hs. The reaction was allowed to cool and the product was distilled at 90° C. at 200 mtorr pressure to give the ethyl 3-(benzylamino)butanoate (6.1 g, 69%) as a clear oil, MS (M+H)+=222. to cool the product was distilled at 90° C. at 200 mtorr pressure

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

Procedure: To a suspension of lithium aluminum hydride (0.76 g, 20 mmol) in cyclopentylmethylether (20 mL) was added a solution of 3-benzylamino-butyric acid ethyl ester (2.10 g, 9.5 mmol) in cyclopentylmethylether (10 mL) dropwise at 0° C. under nitrogen atmosphere. The resulting mixture was warmed to room temperature and stirred for 3 hours. Then small amount of sodium sulfate saturated aqueous solution was added dropwise to quench the reaction at 0° C. and stirred for one hour. The resulting solid material was removed by filtration and the organic solution was concentrated to yield 3-benzylamino-butan-1-ol (1.49 g, 8.3 mmol, 87%) as colorless oil. The oil was used in the subsequent step without further purification. to quench the reaction at 0° C. stirred for one hour The resulting solid material was removed by filtration the organic solution was concentrated

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

Procedure: To a solution of 3-amino-butyric acid ethyl ester (5.00 g, 34.3 mmol), benzaldehyde (4.1 mL, 40 mmol) and acetic acid (1.9 mL, 34 mmol) in 1,2-dichloroethane (120 mL) was added sodium triacetoxyborohydride (17 g, 80 mmol) at room temperature and the mixture was stirred for 20 hours. The reaction mixture was poured into sodium bicarbonate saturated aqueous solution and extracted with chloroform. The organic phase was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant) to afford 3-benzylamino-butyric acid ethyl ester (2.1 g, 9.5 mmol, 28%) as colorless oil. extracted with chloroform The organic phase was dried over anhydrous sodium sulfate concentrated The resulting residue was purified by flash column chromatography on silica gel (chloroform/methanol=10/1 as an eluant)