2-(3-azidopropyl)-2,3-dihydro-1H-isoindole-1,3-dione → 2-(3-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)propyl)-isoindoline-1,3-dione
Reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17])=[N+:2]=[N-:3]>C(O)C#C>[OH:16][CH2:15][C:14]1[N:3]=[N:2][N:1]([CH2:4][CH2:5][CH2:6][N:7]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:17])[CH:13]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-(3-azidopropyl)isoindoline-1,3-dione, 20, (0.62 g, 2.69 mmol) in propargyl alcohol (4 mL) was warmed to 90° C. and stirred for 18 h. The reaction mixture was concentrated under reduced pressure. The crude product containing both regioisomers (˜1:1 ratio) was used in the next step without further purification. ESI+ MS: m/z (rel intensity) 301.1 (100, [M+H]+).
Workup
- concentration