Sodium Bicarbonate → HCID 69782382, compound

Participants

Reaction Steps

4-{[1-(2-Hydroxy-2-hydroxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-3-ylmethyl)-5-oxo-4,4-bis-pyridin-4-ylmethyl-imidazolidin-2-ylidene]-acetyl}-benzonitrile (540 mg, 0.914 mmol), as prepared in example 48, was dissolved in 0.1 N HCl (5 ml). To this solution was added sodium periodate (235 mg, 1.10 mmol). After stirring at ambient temperature for 16 hours, the pH of the reaction was adjusted to 8 using NaHCO3. The reaction was then partitioned between CH2Cl2 and saturated NaHCO3. The CH2Cl2 was dried over Na2SO4, filtered and concentrated under vacuum to give a golden foam which was then chromatographed on silica gel using 60% acetone in hexanes to give 331 mg of the titled compound as a brown foam: C.I. m/z 560 [M+1]; 1H NMR (CDCl3)δ 10.36 (br s, 1H), 8.48 (m, 4H), 7.94 (d, J=8.3 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.14 (m, 4H), 5.49 (s, 1H), 3.46 (m, 2H), 3.29 (m, 2H), 3.09 (m, 2H), 2.52 (m, 2H), 2.24 (m, 1H), 2.18 (m, 1H), 1.49 (m, 1H), 1.29 (s, 3H), 1.19 (d, J=8.9 Hz, 1H), 0.89 (m, 1H), 0.76 (s, 3H).

Provenance & Evidence