Triphenylphosphine → HCID 58804035, compound

Participants

Reaction Steps

Combine [1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-[5-(2-chloro-phenyl)-3-hydroxymethyl-isoxazol-4-yl]-methanone (0.30 g, 0.49 mmol), diphenyl phosphoryl azide (0.13 mL, 0.59 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.09 mL, 0.59 mmole) in THF (2 mL) and stir at RT overnight. Filter off the solid and concentrate the filtrate. Dissolve the crude product in THF (2 mL), add triphenylphosphine (0.16 g, 0.59 mmole), and a few drops of water. Stir the mixture overnight. Purify the resulting amine by sequentially passing through a short silica gel column (gradient elution with EtOAc, 2% MeOH in EtOAc, 5% MeOH/2% NH4OH(aq) in EtOAc), a SCX column (elution with 1:1 MeOH/CH2Cl2 and then 3.5 M NH3 in MeOH) and again a short silica gel column (gradient elution with EtOAc, 5% MeOH/2% NH4OH (aq) in EtOAc) to provide a yellow oil (0.14 g, 47%). 1H NMR (400 MHz, CDCl3) δ 4.07 (s, 2H), 5.45 (s, 2H), 7.18–7.25 (m, 3H), 7.30–7.40 (m, 3H), 7.44 (t, J=7.42 Hz, 1H), 7.74 (d, J=7.62 Hz, 1H), 7.87 (s, 1H), 8.81 (m, 2H); MS (ESI) m/z 607.1 (M+1).

Provenance & Evidence