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0 °C

Diethyl cyanomethyl phosphonate (0.86 ml, 4.4 mmol) was dissolved in dry THF (50 ml) and the solution cooled to 0° C. Sodium hydride (205 mg of a 60% suspension in parrafin oil, 5.1 mmol) was then added cautiously and the reaction stirred for 30 min. The reaction mixture was then cooled to −78° C. and a solution of 1-tert-butyl 2-methyl (2S)-4oxo-1,2-pyrrolidinedicarboxylate (1.0 g, 4.1 mmol) in dry THF (5 ml) was added dropwise. The reaction was then allowed to reach room temperature. Saturated aqueous ammonium chloride solution (15 ml) was then added, followed by ethyl acetate (100 ml). (The organic layer was removed, and the aqueous washed with ethyl acetate (3×5 ml). The combined organic layers were dried with brine and magnesium sulfate before filtering and removal of solvent. Silica gel chromatography, eluting with 35% ethyl acetate in hexanes gave the desired compound (860 mg, 80%) as an off-white wax.

1. temperatureThe reaction mixture was then cooled to −78° C.
2. customto reach room temperature
3. custom(The organic layer was removed
4. washthe aqueous washed with ethyl acetate (3×5 ml)
5. dry with materialThe combined organic layers were dried with brine and magnesium sulfate
6. filtrationbefore filtering
7. customremoval of solvent
8. washSilica gel chromatography, eluting with 35% ethyl acetate in hexanes