2-Methyl-2-butene → HCID 53802001, compound

Participants

Reaction Steps

A solution of sodium chlorite (80%; 131 mg, 1.16 mmol) and sodium phosphate monobasic monohydrate (160 mg, 1.16 mmol) in water (1.1 mL) was added to a solution of (R)-4-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]phenylacetaldehyde from Step 5 (371 mg, 0.893 mmol) and 2-methyl-2-butene (665 μL, 6.25 mmol) in t-BuOH (8 mL). The reaction mixture was stirred at room temperature for 1.5 h before 25% aqueous NH4OAc buffer was added (a few drops of acetic acid were necessary to bring the pH at 7). The mixture was then extracted with EtOAc (2×), and the combined organics were washed successively with 25% aqueous NH4OAc buffer, water and brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica (EtOAc containing 0.5% AcOH). Residual AcOH was co-evaporated with toluene (2×) to afford the title compound as a white foam (319 mg, 83%). 1H NMR (400 MHz, acetone-d6): δ 1.50-1.61 (m, 2H), 1.63-1.88 (m., 6H), 3.40 (d; 2H), 3.54 (s, 2H), 3.70 (s, 3H), 4.34 (t, J=8 Hz, 1H), 4.75 (m, 1H), 6.78 (m, 2H), 6.90 (s, 1H), 7.15 (d, J=6 Hz, 2H), 7.20 (d, J=8 Hz, 2H), 7.30 (d, J=8 Hz, 2H), 8.33 (d, J=5 Hz, 2H).

Provenance & Evidence