Hydrogen Peroxide → HCID 22467278, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of a mixture of [1-(tert-butyldiphenylsilyloxy)-8,9-dihydro-7H-benzocyclohepten-6-yl]methanol and [1-(tert-butyldiphenylsilyloxy)-8,9-dihydro-5H-benzocyclohepten-6-yl]methanol (1.10 g) in THF (10 ml) was added borane-tetrahydrofuran complex (1M THF solution, 7.71 ml) at −30 to −20° C. The mixture was stirred at the same temperature for 30 minutes, and then at room temperature for 18 hours. The reaction mixture was cooled to 5° C. After addition of borane-tetrahydrofuran complex (1M THF solution, 2.57 ml), the mixture was stirred at room temperature for 3 hours. After addition of 2N NaOH solution (2.59 ml) and 30% H2O2 solution (1.76 ml) at 5° C., the resultant was stirred at room temperature for 3 hours. The mixture was extracted with EtOAc. The organic layer was washed with water and then brine. It was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 3:2 to 1:2) to give first (5RS,6RS)-1-(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (719.8 mg) as an amorphous solid and then (6SR,7RS)-1-(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-ol (181.4 mg) as an amorphous solid.

Provenance & Evidence