Sodium Azide → HCID 54675652, compound

Participants

Reaction Steps

To (bromomethyl)cyclopropane (150 mg, 0.822 mmol) in DMF (2492 μl) was added sodium azide (50.2 mg, 0.772 mmol) in a 4 mL vial wrapped in aluminum foil. The solution was left to stir for 16 hours at rt. To the azide solution was added water (1.5 mL), the intermediate from Step C (100 mg, 0.249 mmol), copper(II) sulfate (15.91 mg, 0.100 mmol) and sodium ascorbate (49.4 mg, 0.249 mmol). The solution was heated to 40° C. and stirred for an additional 24 h. The reaction was then filtered through a pad of Celite™ (diatomaceous earth) and partitioned between EtOAc and water. The organic layer was separated, dried (sodium sulfate) and concentrated in vacuo under vacuum. Purification by silica gel column chromatography using a hexanes/EtOAc gradient afforded the product as a white solid. Chiral separation using SFC provided both enantiomers of the title compound. 1H NMR (500 MHz, CHCl2-d): δ 8.86 (dd, J=8.06, 1.59 Hz, 1H); 8.58 (dd, J=4.52, 1.57 Hz, 1H); 7.71 (s, 1H); 7.22 (dd, J=8.08, 4.50 Hz, 1H); 4.90 (dd, J=9.19, 6.28 Hz, 2H); 4.25-4.13 (m, 2H); 2.95-2.83 (m, 2H); 1.88 (s, 3H); 1.33-1.24 (m, 1H); 0.73-0.68 (m, 2H); 0.45-0.41 (m, 2H). m/z=499.1 (M+H).

Provenance & Evidence