Isopropanol → 1-Tert-butyl 2-methyl 5-hydroxypyrrolidine-1,2-dicarboxylate

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Reaction Steps

To a solution of 5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester, 1, (7.95 g, 32.7 mmol) in THF (65 mL) at −78° C., neat DIBAL-H (12.8 mL, 8.97 g, 63.1 mmol) dissolved in THF (25 mL) is added dropwise. After the consumption of the starting material, the reaction is cautiously quenched with isopropanol (5 mL), potassium sodium tartrate (26 g, 124 mmol) in H2O (160 mL). The resultant slurry is taken up in ether (200 mL) and then extracted with ether (5×250 mL). The ether layers are combined, washed with brine (1×250 mL), dried with MgSO4, and concentrated in vacuo to afford 6.8 g (85% yield) of the desired product as a clear oil which is used without further purification. MS (ESI): m/e=268.03 (M+Na).

Provenance & Evidence