Hydrochloric Acid → 5-Aminomethyl-2-methyl-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

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Reaction Steps

To a solution of 5-(tert-butoxycarbonylamino-methyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.8 g, 4.6 mmol) in methylene chloride (10 μL) was added 4 M hydrogen chloride in dioxane (1.2 mL, 4.8 mmol). The mixture was stirred at room temperature for 1 hour and the formed solid was then filtered. The product was further purified by recrystallization (ethanol and methylene chloride) to give 950 mg (63%) of titled product as a beige solid: mp 260-261° C.; MS(APCI−): m/z 293.1 (M−H); Anal. Calcd for C18H18N2O2.1.06HCl: C, 64.92; H, 5.77; N, 8.41; Cl, 11.29. Found: C, 64.58; H, 5.79; N, 8.31; Cl, 11.38.

Provenance & Evidence