Sodium hydride → [1-(2-Cyanofuran-4-ylmethyl)-2-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester

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Reaction Steps

A solution of (2-oxopyrrolidin-3-(S)-yl)carbamic acid tert-butyl ester (0.78 g, 3.9 mmol) in 40 mL of THF:DMF (5:1) is treated with 3-bromomethylfuran-5-carbonitrile (0.78 g, 3.9 mmol) and sodium hydride (60%) (0.10 g, 4.2 mmol) as described in EXAMPLE 122, Part F. After addition, the solution is allowed to warm to ambient temperatures. Standard workup folowed by chromatography (5-10% MeOH/CH2Cl2) affords [1-(2-cyanofuran-4-ylmethyl)-2-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester (1.05 g, 7.8 mmol) as a white solid. This material is treated with trimethylsilyliodide (0.844 g, 4.22 mmol) and free based with Amberlite (OH) resin to yield the title compound (0.926 g, 4.51 mmol).

Provenance & Evidence