Diglyme → HCID 11676256, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of this cyclohexene (110 mg, 0.27 mmol) in 2 ml of diglyme at 0° C. was added dropwise a borane-THF complex solution (1.0 M, 325 μL, 0.325 mmol, 1.5 eq). The resulting solution was stirred for 4 h at 0° C. THF was removed and TAO (trimethyl amine N-oxide, 90 mg, 0.81 mmol) was added. The mixture was heated and refluxed for 2 h. The resulting mixture was cooled to room temperature, extracted with EtOAc (4×40 ml) and dried over MgSO4. The residue was separated by flash chromatography on silica, then was purified by HPLC (Cyclohexane/EtOAc: 9:1) to afford compound 3.2.c (R=Me, P=TBDPS, A=COOCH3) (46 g, 40.5%) as a colorless oil.

Provenance & Evidence