Trifluoroacetic acid → 1-benzyl-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one

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Reaction Steps

TFA (7.8 g, 68.0 mmol) was added dropwise at 0° C. to a solution of tert-butyl 1-benzyl-3-(S)-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (1.5 g, 3.5 mmol) in CH2Cl2 (10 ml) and the mixture was stirred at this temperature for 15 min. After warming to RT, the reaction solution was stirred for a further 2.5 h. Subsequently, the reaction solution was adjusted to pH 7-8 using aqueous saturated NaHCO3 solution, the organic phase was separated off and the aqueous phase was extracted with CH2Cl2 (2×10 ml). The combined organic phase was dried over Na2SO4, filtered and the solvent was distilled off. The workup was carried out by means of column chromatography and afforded 1-benzyl-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one in a yield of 655 mg (58%).

Provenance & Evidence