ethyl 2-(cyclopropylamino)acetate

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

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

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

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

Procedure: Bromoacetic acid ethyl ester (14.2 g, 9.37 ml, 84.8 mmol) was added dropwise to a soln. of cyclopropylamine (19.4 g; 23.5 ml, 0.34 mol) in EtOH (100 ml), while cooling with ice. The reaction mixture was stirred at RT for 18 h and then concentrated i. vac. Water was added to the residue and the mixture was extracted with CHCl3 (5×100 ml). The combined organic phases were washed with half-saturated sodium chloride soln., dried with Na2SO4 and concentrated i. vac. The crude product was distilled at approx. 85° C. under 24 mbar. Yield: 12.03 g (99%) concentrated i Water was added to the residue the mixture was extracted with CHCl3 (5×100 ml) The combined organic phases were washed with half-saturated sodium chloride soln , dried with Na2SO4 concentrated i The crude product was distilled at approx. 85° C. under 24 mbar

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

Procedure: Boc-N-Cyclopropylglycine was prepared from N-cyclopropylglycine ethyl ester, ethyl bromoacetate and cyclopropylamine (similar to J. W. Skiles et al., J. Med. Chem. 35 (1992) 641) and then converted under standard conditions into the Boc-protected form, then hydrolyzed with MeOH/2N NaOH and finally acidified with 1N HCl.

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

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

Procedure: Cyclopropylamine (12.1 mL, 175 mmol) and TEA (42 mL, 385 mmol) were combined at 0° C. in 350 mL CH2Cl2, then ethyl bromoacetate (19.4 mL, 175 mmol) was added dropwise. The reaction was warmed to RT for 3 h, then diluted with additional CH2Cl2, washed with water, sat. NaHCO3, and brine, dried (Na2SO4), filtered and concentrated. Flash filtration (silica, 30% EtOAc/hexane) provided 7-2 as a light yellow oil. washed with water, sat. NaHCO3, and brine dried (Na2SO4) filtered concentrated Flash filtration (silica, 30% EtOAc/hexane)

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

Procedure: To a vigorously stirred solution of 4.9 g (34 mmol) of cyclopropylamino-acetic acid ethyl ester in 50 ml of CH2Cl2 and 25 ml of saturated sodium hydrogen carbonate was added a solution of 8.4 g (37 mmol) of 4-(trifluoromethoxy)benzoyl chloride in 10 ml of CH2Cl2 and the reaction stirred for 1 h. The organic phase was then separated, dried with sodium sulfate and concentrated. Purification by flash column chromatography [n-heptane/EtOAc 1:9 to 3:7] afforded 8.9 g (80%) of the title compound as a colorless oil. MS: 332.1 (MH+). The organic phase was then separated dried with sodium sulfate concentrated Purification by flash column chromatography [n-heptane/EtOAc 1:9 to 3:7]

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

Procedure: To a solution of 10 g (0.18 mol) of cyclopropylamine in 50 ml of EtOH was added 7 g (0.04 mol) of ethylbromoacetate and the reaction stirred for 1 h. The reaction was then evaporated to dryness, redissolved in CH2Cl2 washed with water, dried over sodium sulfate and concentrated to afford 6 g (quant.) of the title compound as a colorless oil. MS: 144.1 (MH+). The reaction was then evaporated to dryness redissolved in CH2Cl2 washed with water dried over sodium sulfate concentrated

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

Procedure: Bromoacetic acid ethyl ester (14.2 g, 9.37 ml, 84.8 mmol) was added dropwise to a soln. of cyclopropylamine (19.4 g; 23.5 ml, 0.34 mol) in EtOH (100 ml), while cooling with ice. The reaction mixture was stirred at RT for 18 h and then concentrated i. vac. Water was added to the residue and the mixture was extracted with CHCl3 (5×100 ml). The combined organic phases were washed with half-saturated sodium chloride soln., dried with Na2SO4 and concentrated i. vac. The crude product was distilled at approx. 85° C. under 24 mbar. Yield: 12.03 g (99%) concentrated i Water was added to the residue the mixture was extracted with CHCl3 (5×100 ml) The combined organic phases were washed with half-saturated sodium chloride soln , dried with Na2SO4 concentrated i The crude product was distilled at approx. 85° C. under 24 mbar

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

Procedure: Boc-N-Cyclopropylglycine was prepared from N-cyclopropylglycine ethyl ester, ethyl bromoacetate and cyclopropylamine (similar to J. W. Skiles et al., J. Med. Chem. 35 (1992) 641) and then converted under standard conditions into the Boc-protected form, then hydrolyzed with MeOH/2N NaOH and finally acidified with 1N HCl.

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

Procedure: Boc-N-Cyclopropylglycine was prepared from N-cyclopropylglycine ethyl ester, ethyl bromoacetate and cyclopropylamine (similar to J. W. Skiles et al., J. Med. Chem. 35 (1992) 641) and then converted under standard conditions into the Boc-protected form, then hydrolyzed with MeOH/2N NaOH and finally acidified with 1N HCl.