Tetrahydrofuran → HCID 69154999, compound

Participants

Reaction Steps

Add TMEDA (8.3 mL, 55.0 mmol) to a solution of phenyl-carbamic acid tert-butyl ester (4.83 g, 25.0 mmol) in THF (50 mL) at −40° C. in a flame dried flask. After 5 min., add s-BuLi (43 mL, 55.0 mmol, 1.3 M in cyclohexane) dropwise over 10 min. Allow solution to warm to RT. After 30 min., add saturated aqueous NH4Cl solution (approx. 15 mL) and stir for 30 min. Concentrate, partition between 20% i-PrOH/CHCl3 and saturated aqueous NaHCO3 solution and separate. Wash organic layer with brine, dry over MgSO4, and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-20% ethyl acetate/hexanes to afford the title compound: TLC (10% ethyl acetate/hexanes) Rf=0.20.

Provenance & Evidence