2-Dimethylaminopyridine → N-Cbz-2-aminoisobutyric acid 2,2,5,5-tetramethylcyclopentyl ester

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Reaction Steps

To a stirred solution of 2 g (0.008 mol) of N-Cbz-2-aminoisobutyric acid in dry Cl(CH2)2Cl containing 1.9 g dicyclohexylcarbodiimide and 0.1 g dimethylaminopyridine (DMAP), all at 0° C., is added, via an addition funnel, 1.3 g of 2,2,5,5-tetramethylcyclopentanol dissolved in CH2Cl2. After stirring for 4 days, the mixture is filtered, and the filtrate is washed with 5% HCl (1×50 ml), saturated NaHCO3 (1×50 ml), and water (1×50 ml). The organic layer is separated, dried over MgSO4 and evaporated to yield N-Cbz-2-aminoisobutyric acid 2,2,5,5-tetramethylcyclopentyl ester.

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