benzyl 2-(cyclopentylamino)acetate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of Benzyl-2-bromoacetate (3.30 ml, 20.0 mmol) in 20 mL CH2 Cl2 was added drop-wise to a solution of cyclopentylamine (8.60 g, 100 mmol) in 20 mL of CH2Cl2, with stirring at 0° C. On completion of the addition of benzyl-2-bromoacetate, the reaction was stirred at room temperature 17 hours. The organic solvent was removed in vacuo and the residue was taken up in ethyl acetate and washed with saturated Na2CO3 solution. The solution was extracted with 1N HCl . The aqueous layer was made basic with Na2CO3 and extracted with chloroform. The organic layer was dried (MgSO4) and evaporated. The residue was purified by silica gel flash column chromatography, eluting sequentially with hexane and hexane/ethyl acetate (1:1, v/v) to yield 2.3 g (50.0%) of the title compound as an oil. 1 H NMR (CDCl3) δ 6 1.25-1.85 (m, 9H); 3.0-3.12 (m, 1H); 3.43 (s, 2H); 5.15 (s, 2H); 7.27-7.42 (m, 5H); 13C NMR (CDCl3) δ 23.72, 32.71, 49.53, 59.03, 66.24, 128.1, 128.32, 135.42, 172.29. the reaction was stirred at room temperature 17 hours The organic solvent was removed in vacuo washed with saturated Na2CO3 solution The solution was extracted with 1N HCl extracted with chloroform The organic layer was dried (MgSO4) evaporated The residue was purified by silica gel flash column chromatography eluting sequentially with hexane and hexane/ethyl acetate (1:1