Water → 1,2-Pyrrolidinedicarboxylic acid, 4-(methoxymethyl)-, 1-(1,1-dimethylethyl) ester, (2S,4S)-

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Reaction Steps

A solution of (2S,4S)-1-tert-butyl 2-methyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate (18 g, 66.91 mmol) and lithium hydroxide (3.37 g, 80.3 mmol) in THF (50 mL), methanol (50 mL), and water (50 mL) was stirred at RT for 2 h. The reaction mixture was adjusted to ph 6 and extracted with 10:1 DCM:methanol. The organic phase was dried over sodium sulfate and concentrated to provide the title intermediate (17 g, 84% yield) as a colorless oil). 1H NMR (400 MHz, CDCl3): δ(ppm) 1.398-1.451 (d, 9H, J=21.2 Hz), 1.625-1.754 (m, 1H), 2.226-2.652 (m, 3H), 3.251-3.458 (m, 1H), 3.316 (s, 3H), 3.316-3.462 (m, 2H), 3.556-3.750 (m, 2H), 4.405-4.445 (m, 1H), 7.652 (s, 1H).

Provenance & Evidence