Tetrahydrofuran → HCID 51557134, compound

Participants

Reaction Steps

To a solution of (4R)-6-iodochroman-4-ol (6.85 9, 24.81 mmol) and toluene (100 mL) under nitrogen at 0° C. was added diphenylphosphoryl azide (6.42 mL, 29.76 mmol). To this mixture was added a chilled solution of DBU (4.45 mL, 29.76 mmol) as a toluene solution (25 mL) via syringe. Reaction mixture was allowed to warm to ambient temperature overnight. Azide solution was filtered through silica gel using 6:1 hexanes:EtOAc as eluant. Filtrate was concentrated in vacuo, then dissolved in anh. THF (100 mL) to which was added 1.0M Me3P in THF (29.76 mL, 29.76 mmol). After 1 h, deionized H2O (5 mL) was added and reaction mixture was stirred overnight under nitrogen. Concentrated in vacuo, dissolved in EtOAc, washed with 10% NaHCO3, brine, then the organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give (4S)-6-iodochroman-4-amine as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.70 (s, 2H), 1.86 (m, 1H), 2.13 (m, 1H), 4.03 (t, J=5 Hz, 1H), 4.23 (m, 2H), 6.60 (d, J=9 Hz, 1H), 7.42 (d, J=9 Hz, 1H), 7.64 (s, 1H). MS (ESI+) for C9H10INO m/z 258.8 (M+H)+.

Provenance & Evidence