Imidazole → (2S,4R)-1-tert-Butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate

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Reaction Steps

To a solution of (2S,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (5.12 g, 20.8 mmol) in DMF (40 mL), imidazole (2.84 g, 41.7 mmol) and tert-butyldimethylchlorosilane (3.46 g, 22.9 mmol) were added sequentially and the mixture was stirred at ambient temperature for about 2 hours. The DMF was removed under reduced pressure and the residue partitioned between water (150 mL) and ether (150 mL). The organic phase was washed with 1N aqueous phosphoric acid (3×100 mL), water (2×100 mL), sodium bicarbonate saturated solution (2×100 mL) and brine (100 mL). The organic phase was dried with magnesium sulfate and concentrated to yield (2S,4R)-1-tert-butyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate (5.44 g, 15.1 mmol) as a colorless oil. RP-HPLC (Table 1, Method f) Rt 6.49 min.

Provenance & Evidence