Sodium Azide → HCID 86732135, compound

Participants

Reaction Conditions

Reaction Steps

A sealable vial was charged with (+)-sodium L-ascorbate (0.026 g, 0.13 mmol, Aldrich), sodium azide (0.102 g, 1.56 mmol, Aldrich), copper(I) iodide (0.026 g, 0.13 mmol, Acros), and tert-butyl ((4S,6S)-4-(6-bromo-3-fluoropyridin-2-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate (7i, 0.238 g, 0.52 mmol). The sealed vial was evacuated and backfilled with Nitrogen. EtOH (2.5 mL) was added followed by water (1 mL) and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.021 mL, 0.130 mmol, Aldrich). The reaction mixture was heated to 70° C. for 3 hs. The cooled reaction mixture was partitioned between NH4Cl/NH4OH (9:1) (10 mL) and EtOAc (10 mL). The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The crude material was purified via silica gel flash chromatography (gradient 10-50% EtOAc in hexanes) to afford the title compound as a white solid (0.119 g, 0.3 mmol, 58% yield). MS m/z=393.2 [M+H]+. Calculated for C16H20F4N4O3: 392.3

Provenance & Evidence