Hydrogen Peroxide → HCID 67956886, compound

Participants

Reaction Steps

L-Selectride® (1M in THF; 69.0 mL; 69.0 mm0l) is dropped into a stirred solution of (2S*,4R*)-4-{[tert-butyl(diphenyl)silyl]oxy}-2-fluorocyclohexanone (example C14; 23.3 g; 62.8 mmol) in dry THF (230 mL) at −15° C. The reaction mixture is stirred over night and cooled to 0° C. before careful addition of ice cold water (100 mL), followed by dropwise addition of H2O2 (30% solution in water; 39.0 mL). After 30 min. saturated Na2SO3-solution (80 mL) is dropwise added at 0° C. tert-BuOMe (300 mL) is added, the organic layer is separated and concentrated under reduced pressure. The aqueous layer is extracted with tert-BuOMe. All combined organic phases are washed with brine and dried over MgSO4. The solvent is removed under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/AcOEt—10:0 to 9:1) to yield 15.5 g of the title compound as colourless liquid.

Provenance & Evidence