ethyl 2-(propylamino)acetate

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ammonium formate (2 g, 31 mmol) was added to a solution of ethyl 2-[benzylpropylamino]acetate (1.05 g, 4.47 mmol) in ethanol (15 mL) and acetic acid (1 mL). The reaction vessel was then carefully flushed with nitrogen gas. Palladium on carbon (10%, 300 mg) was added in one portion, and the resulting mixture was heated at 80° C., under nitrogen for 3 h. The reaction mixture was allowed to cool to room temperature, and filtered through celite filteraid. The filtrate was concentrated in vacuo, (azeotroping with toluene (20 mL) to remove the acetic acid), to give ethyl 2-(propylamino)acetate as a yellow oil (quantitative crude yield). 1H NMR (CDCl3) δ 4.14 (q, J=7.1 Hz, 2H), 3.30 (s, 2H), 2.60 (dd, J=7.4 Hz, 2H), 1.50 (m, 2H), 1.26 (t, J=7.2 Hz, 3H), 0.89 (t, J=7.4 Hz, 3H). The reaction vessel was then carefully flushed with nitrogen gas Palladium on carbon (10%, 300 mg) was added in one portion to cool to room temperature filtered through celite filteraid The filtrate was concentrated in vacuo (azeotroping with toluene (20 mL) to remove the acetic acid), to give

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ammonium formate (2 g, 31 mmol) was added to a solution of ethyl 2-[benzylpropylamino]acetate (1.05 g, 4.47 mmol) in ethanol (15 mL) and acetic acid (1 mL). The reaction vessel was then carefully flushed with nitrogen gas. Palladium on carbon (10%, 300 mg) was added in one portion, and the resulting mixture was heated at 80° C., under nitrogen for 3 h. The reaction mixture was allowed to cool to room temperature, and filtered through celite filteraid. The filtrate was concentrated in vacuo, (azeotroping with toluene (20 mL) to remove the acetic acid), to give ethyl 2-(propylamino)acetate as a yellow oil (quantitative crude yield). 1H NMR (CDCl3) δ 4.14 (q, J=7.1 Hz, 2H), 3.30 (s, 2H), 2.60 (dd, J=7.4 Hz, 2H), 1.50 (m, 2H), 1.26 (t, J=7.2 Hz, 3H), 0.89 (t, J=7.4 Hz, 3H). The reaction vessel was then carefully flushed with nitrogen gas Palladium on carbon (10%, 300 mg) was added in one portion to cool to room temperature filtered through celite filteraid The filtrate was concentrated in vacuo (azeotroping with toluene (20 mL) to remove the acetic acid), to give

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

Procedure: 7.16 g (49.4 mM) of ethyl N-(n-propyl)glycinate and 6.4 ml (50 mM) of ethyl malonyl chloride were added simultaneously to an ice-cold solution of 6.9 g (50 mM) of potassium carbonate in 15 ml water overlaid with 50 ml ether. The cooling bath was removed and the reaction warmed to ambient temperature stirring for 1.5 hours. The aqueous phase was acidified to pH 4 with concentrated HCl and the layers separated. The aqueous phase was extracted with 15 ml ether and the combined ether layer washed with brine and dried over anhydrous Na2SO4 then concentrated to yield 11.8 g of the desired product as a pale yellow oil. The cooling bath was removed the layers separated The aqueous phase was extracted with 15 ml ether the combined ether layer washed with brine dried over anhydrous Na2SO4 then concentrated

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

Procedure: 5.53 ml (50 mM) of ethyl bromoacetate were added dropwise to a solution of 20.5 ml (250 mM) of n-propylamine in 50 ml of CH2Cl2 at 0°. The reaction mixture was then warmed to room temperature and stirred for 1 hour, then concentrated to remove volatiles through a short path distillation head at atmospheric pressure. The residual liquid was taken up in ether and washed with saturated aqueous NaHCO3. The layers were separated and the ether layer was washed once with brine then dried over anhydrous MgSO4. The ether was removed to yield 7.16 g of ethyl N-(n-propyl)-glycinate as a pale yellow liquid. concentrated to remove volatiles through a short path distillation head at atmospheric pressure washed with saturated aqueous NaHCO3 The layers were separated the ether layer was washed once with brine then dried over anhydrous MgSO4 The ether was removed

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ammonium formate (2 g, 31 mmol) was added to a solution of ethyl 2-[benzylpropylamino]acetate (1.05 g, 4.47 mmol) in ethanol (15 mL) and acetic acid (1 mL). The reaction vessel was then carefully flushed with nitrogen gas. Palladium on carbon (10%, 300 mg) was added in one portion, and the resulting mixture was heated at 80° C., under nitrogen for 3 h. The reaction mixture was allowed to cool to room temperature, and filtered through celite filteraid. The filtrate was concentrated in vacuo, (azeotroping with toluene (20 mL) to remove the acetic acid), to give ethyl 2-(propylamino)acetate as a yellow oil (quantitative crude yield). 1H NMR (CDCl3) δ 4.14 (q, J=7.1 Hz, 2H), 3.30 (s, 2H), 2.60 (dd, J=7.4 Hz, 2H), 1.50 (m, 2H), 1.26 (t, J=7.2 Hz, 3H), 0.89 (t, J=7.4 Hz, 3H). The reaction vessel was then carefully flushed with nitrogen gas Palladium on carbon (10%, 300 mg) was added in one portion to cool to room temperature filtered through celite filteraid The filtrate was concentrated in vacuo (azeotroping with toluene (20 mL) to remove the acetic acid), to give

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

Procedure: 7.16 g (49.4 mM) of ethyl N-(n-propyl)glycinate and 6.4 ml (50 mM) of ethyl malonyl chloride were added simultaneously to an ice-cold solution of 6.9 g (50 mM) of potassium carbonate in 15 ml water overlaid with 50 ml ether. The cooling bath was removed and the reaction warmed to ambient temperature stirring for 1.5 hours. The aqueous phase was acidified to pH 4 with concentrated HCl and the layers separated. The aqueous phase was extracted with 15 ml ether and the combined ether layer washed with brine and dried over anhydrous Na2SO4 then concentrated to yield 11.8 g of the desired product as a pale yellow oil. The cooling bath was removed the layers separated The aqueous phase was extracted with 15 ml ether the combined ether layer washed with brine dried over anhydrous Na2SO4 then concentrated

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

Procedure: 5.53 ml (50 mM) of ethyl bromoacetate were added dropwise to a solution of 20.5 ml (250 mM) of n-propylamine in 50 ml of CH2Cl2 at 0°. The reaction mixture was then warmed to room temperature and stirred for 1 hour, then concentrated to remove volatiles through a short path distillation head at atmospheric pressure. The residual liquid was taken up in ether and washed with saturated aqueous NaHCO3. The layers were separated and the ether layer was washed once with brine then dried over anhydrous MgSO4. The ether was removed to yield 7.16 g of ethyl N-(n-propyl)-glycinate as a pale yellow liquid. concentrated to remove volatiles through a short path distillation head at atmospheric pressure washed with saturated aqueous NaHCO3 The layers were separated the ether layer was washed once with brine then dried over anhydrous MgSO4 The ether was removed

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

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

Procedure: 7.16 g (49.4mM) of ethyl N-(n-propyl)glycinate and 6.4 ml (50 mM) of ethyl malonyl chloride were added simultaneously to an ice-cold solution of 6.9 g (50 mM) of potassium carbonate in 15 ml water overlaid with 50 ml ether. The cooling bath was removed and the reaction warmed to ambient temperature stirring for 1.5 hours. The aqueous phase was acidified to pH 4 with concentrated HCl and the layers separated. The aqueous phase was extracted with 15 ml ether and the combined ether layer washed with brine and dried over anhydrous Na2SO4 then concentrated to yield 11.8 g of the desired product as a pale yellow oil. The cooling bath was removed the layers separated The aqueous phase was extracted with 15 ml ether the combined ether layer washed with brine dried over anhydrous Na2SO4 then concentrated

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

Procedure: 5.53 ml (50 mM) of ethyl bromoacetate were added dropwise to a solution of 20.5 ml (250 mM) of n-propylamine in 50 ml of CH2Cl2 at 0°. The reaction mixture was then warmed to room temperature and stirred for 1 hour, then concentrated to remove volatiles through a short path distillation head at atmospheric pressure. The residual liquid was taken up in ether and washed with saturated aqueous NaHCO3. The layers were separated and the ether layer was washed once with brine then dried over anhydrous MgSO4. The ether was removed to yield 7.16 g of ethyl N-(n-propyl)-glycinate as a pale yellow liquid. concentrated to remove volatiles through a short path distillation head at atmospheric pressure washed with saturated aqueous NaHCO3 The layers were separated the ether layer was washed once with brine then dried over anhydrous MgSO4 The ether was removed

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

Procedure: 7.16 g (49.4 mM) of ethyl N-(n-propyl)glycinate and 6.4 ml (50 mM) of ethyl malonyl chloride were added simultaneously to an ice-cold solution of 6.9 g (50 mM) of potassium carbonate in 15 ml water overlaid with 50 ml ether. The cooling bath was removed and the reaction warmed to ambient temperature stirring for 1.5 hours. The aqueous phase was acidified to pH 4 with concentrated HCl and the layers separated. The aqueous phase was extracted with 15 ml ether and the combined ether layer washed with brine and dried over anhydrous Na2SO4 then concentrated to yield 11.8 g of the desired product as a pale yellow oil. The cooling bath was removed the layers separated The aqueous phase was extracted with 15 ml ether the combined ether layer washed with brine dried over anhydrous Na2SO4 then concentrated