Tetrahydrofuran → HCID 51557134, compound

To a solution of (4R)-6-iodochroman-4-ol (6.85 g, 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, 2 H), 1.86 (m, 1 H), 2.13 (m, 1 H), 4.03 (t, J=5 Hz, 1 H), 4.23 (m, 2 H), 6.60 (d, J=9 Hz, 1 H), 7.42 (d, J=9 Hz, 1 H), 7.64 (s, 1 H). MS (ESI+) for C9H10INO m/z 258.8 (M+H)+.

1. customReaction mixture
2. filtrationAzide solution was filtered through silica gel using 6:1 hexanes
3. concentrationFiltrate was concentrated in vacuo
4. dissolutiondissolved in anh. THF (100 mL) to which
5. customreaction mixture
6. concentrationConcentrated in vacuo
7. dissolutiondissolved in EtOAc
8. washwashed with 10% NaHCO3, brine
9. dry with materialthe organic layers were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-5fb5810a372f4dc186570b7e5e5444aa

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544717B2