Diisopropylethylamine → (3R,4R)-di-tert-butyl 4-(benzyloxycarbonylamino)pyrrolidine-1,3-dicarboxylate

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Reaction Steps

To a solution of (3R,4R)-di-tert-butyl 4-aminopyrrolidine-1,3-dicarboxylate (Org. Biomol. Chem. 2004, 2, 2763-2776) (765 mg, 2.67 mmol) and Hunig's base (465 uL, 2.67 mmol) in N,N-dimethylformamide (5 mL) was added Cbz succinimide (665 mg, 2.67 mmol). The mixture was stirred for 3 hours and partitioned between EtOAc and water. The organic layer was washed repeatedly with brine, dried (Na2SO4) and concentrated to a clear oil (1.18 g, quantitative yield). MS (DCI/NH4) m/z=438 (M+NH4)+.

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