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Add sodium azide (2.14 g, 32.92 mmol) to a solution of 2-bromo-2'- methoxyacetophenone (5.01 g, 21.87 mmol) in 75 ml of DMSO. Stir the mixture at ambient temperature for 18 hours and dilute it with 250 ml of water. Extract the mixture with ether (3X). Dry the combined organic layers with MGS04. Filter off the drying agent and concentrate in vacuo to afford 3.54 g of 2-AZIDO-1-(2-METHOXYPHENYL)- ethanone. Dissolve 2-azido-l- (2-methoxy-phenyl)-ethanone (3.54 g, 18.5 mmol) in 1328 ml OF MEOH and 9 ml of concentrated HCI. Add 943 mg of 10% Pd/C and expose the reaction mixture to 60 psi of H2 for 5 hours at ambient temperature. Filter the catalyst off through a pad of celite and concentrate the filtrate in vacuo to afford 3.74 g of crude 2- AMINO-1- (2-METHOXYPHENYL)-ETHANONE as the hydrochloride salt. Dissolve 1- [3- (DIMETHYLAMINO) PROPYL]-3-ETHYLCARBODIIMIDE hydrochloride (3.57 g, 18.62 MMOL), 4- (DIMETHYLAMINO) pryidine (463.8 mg, 3.79 mmol) and adipic acid monomethyl ester (2.97 g, 18. 55 mmol) in 100 mL of CH2CL2 and allow it to stir at room temperature for 45 minutes. Add crude 2-amino-l- (2-methoxy-phenyl)-ethanone hydrochloride (3.74 g, 18.55 mmol) and triethylamine (3.75 g, 37.1 mmol) to the reaction mixture and allow it to stir at ambient temperature for 22 hours. Dilute the reaction with 200 mL of CH2C12 and wash it with 1 N HC1 (2X), saturated aqueous NAHCO3 (2X) and brine (1X). Dry the organic layer with MGS04. Filter the drying agent and concentrate in vacuo to afford 4.57 g of the titled product (80%): mass spectrum: M/Z = 308.1 (M+H).
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