Trimethylsilyl iodide → 5-(3-aminomethyl-cyclohexyl)-3-methyl-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-4-one hydroiodide

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Reaction Steps

Dissolve [3-(3-methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester (0.42 g, 0.00093 mol) in dry dichloromethane. Add iodotrimethylsilane (0.33 mL, 0.0023 mol) and stir overnight at ambient temperature. Quench the mixture with methanol (5 mL) and concentrate in vacuo. Take up the resulting residue in minimal dichloromethane and add diethyl ether. Concentrate and titrate from dichloromethane/diethyl ether to form a dark solid. Decant the solvent and the dry in vacuo to give a near quantitative amount of the crude amine salt as a dark solid and used directly without purification. MS(ES): (M+1)+ 313.2, 314.2 m/z.

Provenance & Evidence