Sodium Hydroxide → (2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid

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Reaction Steps

To a stirred solution of N-tert-butoxycarbonyl-2-methylproline methyl ester (3.20 g, 0.0131 mol) in THF (20 mL) was added 1 N NaOH (15.7 mL) at room temp. After the resulting mixture was stirred for 24 hr, the mixture was diluted with water and washed with EtOAc. The separated aqueous layer was acidified by the addition of 1 N HCl, and extracted with EtOAc. The extract was dried over Na2SO4 and evaporated in vacuo to afford 1.71 g(57%) N-tert-butoxycarbonyl-2-methylproline as a yellow syrup. 1H-NMR (CDCl3) δ 1.42 (s, 9H), 1.48 (s, 3H), 1.88–2.31 (m, 4H), 3.34–3.57 (m, 2H), 9.35 (br s, 1H)

Provenance & Evidence