Sodium Iodide → HCID 67187886, compound

Participants

Reaction Conditions

Reaction Steps

Compound B4 (176 mg, 0.5 mmol) was dissolved in anhydrous THF (0.5 mL). The solution was cooled to 0° C. and BH3-THF (2.0 M, 0.25 mL, 0.5 mmol) was added via a syringe. The solution was then stirred at room temperature for 1 h. Methanolic NaOAc (3.0 mL, 1.0 M, 3.0 mmol), aqueous NaI (3.0 mL, 1.0 M, 3.0 mmol) and methanolic chloramine-T (6.0 mL, 0.5 M, 3.0 mmol) were added sequentially to the organoborane solution at room temperature. The reaction mixture were stirred for 10 min at room temperature and then quenched with aqueous Na2S2O3 (1.0 M). The mixture was partitioned between Et2O (50 mL) and H2O (50 mL) and the organic layer was washed with brine (30 mL) before drying over Na2SO4. The solvent was evaporated and the residue was subjected to silica chromatography (CH2Cl2/hexanes, 2/100 to 7/100) to yield compound 1b (85 mg). The yield was 35%. 1H NMR (200 MHz, CDCl3) δ 7.37 (m, 10H), 5.11 (s, 4H), 3.21 (d, 2H, J=8.0 Hz), 2.37 (m, 4H), 1.68 (m, 4H), 1.20 (m, 1H); 13C NMR (50 MHz, CDCl3) δ 173.2, 136.3, 129.1, 128.8, 66.9, 37.5, 31.8, 29.9, 14.5; MS (MALDI-TOF) calcd (M+Na+) 503.3, found 503.8.

Provenance & Evidence