Iodine → HCID 86675827, compound

Participants

Reaction Steps

The compound (119 mg) obtained in Step 2 of this Reference Example was dissolved in toluene (5 mL). To this solution, a solution of sodium bicarbonate (166 mg) in water (4 mL), iodine (305 mg), and 2,2,6,6-tetramethyl-1-piperidinyloxy (11 mg) were added in this order, and the mixture was stirred at room temperature for 12 hours. To the reaction solution, saturated aqueous sodium thiosulfate was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=1/1-1/2) to obtain the title compound (115 mg, diastereomeric mixture, trans:cis=1:1). 1H-NMR (CDCl3) δ: 0.86 (1.5H, t, J=7.3 Hz), 0.90 (1.5H, t, J=7.3 Hz), 1.44 (9H, s), 1.51 (1H, dq, J=7.4, 7.4 Hz), 1.59 (1H, dq, J=7.4, 7.4 Hz), 1.87-1.97 (1H, m), 2.04-2.13 (0.5H, m), 2.28-2.38 (1.5H, m), 2.42-2.52 (1H, m), 2.66-2.75 (1H, m), 4.48 (0.5H, tt, J=9.0, 7.8 Hz), 4.72 (0.5H, tt, J=7.8, 7.4 Hz), 7.58 (0.5H, s), 7.61 (0.5H, s), 7.69 (0.5H, s), 7.74 (0.5H, s), 9.87 (0.5H, s), 9.88 (0.5H, s).

Provenance & Evidence