Hydrochloric Acid → (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid

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Reaction Steps

To a solution of (R)-1-tert-butyl 5-methyl 3,3-dimethyl-1,3-azasilolidine-1,5-dicarboxylate (3.1 g, 11.3 mmol, Eur. J. Org. Chem., 807-811 (2000)) in THF (10 mL) and MeOH (15 mL) was added a solution of lithium hydroxide monohydrate (2.9 g, 68 mmol) in water (15 mL). The resulting reaction mixture was stirred at rt for 4 h and the pH was adjusted to 1 using 1N HCl. The resulting aqueous layer was extracted with ethyl ether (2×). The organic solution was dried over MgSO4 and concentrated in vacuo to afford the title compound as a glassy material (2.9 g, 99%). 1H NMR (400 MHz, CDCl3) δ 4.91-4.53 (m, 1H), 3.06-2.47 (m, 2H), 1.61-1.04 (m, 11H), 0.27 (d, J=6.8 Hz, 6H); MS(ESI+) m/z 260.1 (M+H)+.

Provenance & Evidence