Methyl iodide → 1-(tert-Butyl) 2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

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Reaction Steps

A solution containing 3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (1, 16 g, 71 mmol. See: Hodges, J. A.; Raines, R. T. J. Am. Chem. Soc. 2005, 45, 15923) in DMF (100 mL) was cooled to 0° C. To this solution was added K2CO3 (16 g, 116 mmol) followed by iodomethane (5.4 mL, 87 mmol). The reaction mixture was slowly warmed to ambient temperature over 1 h at which time it became a yellow heterogeneous solution. This mixture was heated at 90° C. for 1 h and then cooled to ambient temperature. The solution was diluted with brine, extracted with diethyl ether, dried over anhydrous Na2SO4, filtered, and concentrated to afford 14.8 g (87%) of 3-hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (2) as a yellow oil (See: Demange, L.; Cluzeau, J.; Menez, A.; Dugave, C. Tetrahedron Lett. 2001, 42, 651).

Provenance & Evidence