Benzyl chloroformate → Z-Pyr-OtBu

Participants

Reaction Conditions

Reaction Steps

To a solution of 1a (2.00 g, 10.8 mmol) in 50 mL THF at −78° C., was added LiHMDS (1M THF, 11.9 mL, 11.9 mmol). The mixture was stirred at −78° C. for 20 min, then Cbz-Cl was added, dropwise over 5 min. The mixture was stirred at −78° for 20 min, then quenched with sat. NH4Cl. The mixture was diluted with H2O and extracted with EtOAc (3×). The organic phase was washed with brine, dried (Na2SO4), and concentrated. The crude product was purified by flash chromatography (30 to 35 to 40% EtOAc/hexanes) to afford 3.12 g (90%) of 8a as a colorless solid.

Provenance & Evidence