Hydrogen Peroxide → HCID 22064361, compound

Participants

Reaction Steps

A solution of Example 25A (1.18 g, 5 mmol) in THF (20 mL) was treated with a solution of 9-BBN (0.5M in THF, 10 mL, 5.0 mmol) via syringe. After stirring at room temperature overnight, the solution was cooled with an ice bath, treated with a solution of NaOH (0.2 g) in water (2 mL), treated dropwise with hydrogen peroxide (30% wt, 0.56 g, 5.0 mmol), and stirred for 3 hours. The mixture was treated with water (50 mL) and ethyl acetate (150 mL) and the organic phase was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 0.55 g (42.8%) of the desired product. MS (DCI/NH3) m/z 275 (M+NH4)+; 1H NMR indicated two isomers in ˜4:1 ratio. The spectrum of the major isomer (300 MHz, CDCl3) δ 7.79 (d, J=2.4 Hz, 1H), 7.46 (dd, J=8.8, 2.7 Hz, 1H), 7.01 (d, J=8.8 Hz, 1H), 4.95–5.05 (m, 1H), 4.55–4.60 (m, 1H), 1.4–2.30 (m, 7H).

Provenance & Evidence