N-(2-aminoethyl)-2-hydroxybenzamide

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

Procedure: To a solution of N-(2-aminoethyl)-2-hydroxybenzamide (332 mg, 1.85 mmol), dimethoxyacetaldehyde (0.475 mL, 1.85 mmol) in CH2Cl2 (10 mL) was added sodium triacetoxyboro hydrid (588 mg, 2.80 mmol). The resulting mixture was stirred overnight, then diluted with EtOAc (50 mL), washed with 10 mL of water and then brine, dried over MgSO4, and conc in vacuo to yield 441 mg (97%) of the product as a colorless oil. MS (ESI) 269 (M+H). washed with 10 mL of water brine, dried over MgSO4

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

Procedure: To a stirring solution of [2-(2-hydroxy-benzoylamino)-ethyl]-carbamic acid tert-butyl ester (1.0 g, 3.57 mmol) in CH2Cl2 (20 mL) was added 2 M HCl (10.71 mL, 21.42 mmol). The reaction was stirred for 30 min and then conc in vacuo to yield a white solid. The solid was rinsed with Et2O and dissolved in 20 mL of MeOH. To the solution was added DiaionWaz21 J resin (5 g, Supelco). The solution was stirred for 30 min and then filtered. The filtrate was conc in vacuo to yield 629 mg (98%) of the product as a colorless oil. MS (ESI): 181 (M+H). conc in vacuo to yield a white solid The solid was rinsed with Et2O dissolved in 20 mL of MeOH To the solution was added DiaionWaz21 J resin (5 g, Supelco) The solution was stirred for 30 min filtered

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

Procedure: To a solution of N-(2-aminoethyl)-2-hydroxybenzamide (332 mg, 1.85 mmol), dimethoxyacetaldehyde (0.475 mL, 1.85 mmol) in CH2Cl2 (10 mL) was added sodium triacetoxyboro hydrid (588 mg, 2.80 mmol). The resulting mixture was stirred overnight, then diluted with EtOAc (50 mL), washed with 10 mL of water and then brine, dried over MgSO4, and conc in vacuo to yield 441 mg (97%) of the product as a colorless oil. MS (ESI) 269 (M+H). washed with 10 mL of water brine, dried over MgSO4

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

Procedure: To a stirring solution of [2-(2-hydroxy-benzoylamino)-ethyl]-carbamic acid tert-butyl ester (1.0 g, 3.57 mmol) in CH2Cl2 (20 mL) was added 2 M HCl (10.71 mL, 21.42 mmol). The reaction was stirred for 30 min and then conc in vacuo to yield a white solid. The solid was rinsed with Et2O and dissolved in 20 mL of MeOH. To the solution was added DiaionWaz21 J resin (5 g, Supelco). The solution was stirred for 30 min and then filtered. The filtrate was conc in vacuo to yield 629 mg (98%) of the product as a colorless oil. MS (ESI): 181 (M+H). conc in vacuo to yield a white solid The solid was rinsed with Et2O dissolved in 20 mL of MeOH To the solution was added DiaionWaz21 J resin (5 g, Supelco) The solution was stirred for 30 min filtered