Toluene → HCID 69601022, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-3 (0.15 g, 0.4 mmol) in 8 mL CH2Cl2 was added 1M (R)-CBS in toluene (0.45 mL, 0.45 mmol) and cooled to −40° C. to which a solution of catechol borane (0.13 mL, 1.2 mmol) in CH2Cl2 (1 mL) was added dropwise. The solution was stirred at −40° C. for one hour and allowed to warm up to −20° C. during the following two hours. The reaction mixture was quenched at −20° C. with 1 N HCl and was stirred for 4 hours at room temperature. The phases were separated and the organic phase was sequentially washed with 1N HCl, H2O, 1 N NaOH, brine and dried over Na2SO4, filtered and concentrated in vacuo. The compound was purified by flash chromatography using 40–50% ethyl acetate/hexanes to yield 125 mg of 4-4 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.37–7.21 (m, 5H), 5.84 (dd, 1H), 5.65 (dd, 1H), 4.46 (q, 1H), 4.22 (q, 1H), 3.86–3.35 (m, 2H), 2.97 (dd, 1H), 2.88 (m, 2H), 2.80 (m, 1H), 2.36 (t, 2H), 1.70–1.27 (m, 8H); MS (+ESI): m/z 359.0 (M+1)+.

Provenance & Evidence