Diisobutylaluminum hydride → 2-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl ester

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Reaction Steps

To 2-tert-butoxycarbonylamino-N-methoxy-N-methyl succinamic acid benzyl ester (0.50 g, 1.36 mmol) in THF (5 mL) at −78° C. was added DIBAL-H (0.233 g, 1.67 mmol) dropwise. The mixture was stirred for 1.5 h and monitored by TLC. When completed the reaction was quenched with 5 mL of saturated solution of Rochell salt (KNaC4H4O6.4H2O) (potassium sodium tartrate) and extracted with EtOAc (2×10 mL). The organic layer was washed with H2O, brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound in quantitative yield (0.40 g).

Provenance & Evidence