Hydrogen Peroxide → HCID 70187793, compound

Participants

Reaction Steps

To a solution of 1-[2-(N,N-diphenylcarbamoyloxy)-ethyl]-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthalene (2.0 g) in THF (tetrahydrofuran) (20 ml) was added BH3 (4.8 ml, 1M solution in THF) at 0° C. under N2. After being stirred for 12 hours at the room temperature, 2N-NaOH solution (1.5 ml) and H2O2 (1.0 ml, 35% solution) were added to the solution and stirred for 4 hours. The mixture was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (trans)-1-[2-(N,N-diphenylcarbamoyl-oxy)ethyl]-2-hydroxy-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.1 g).

Provenance & Evidence