Dichloromethane methanol → (R)-methyl 6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoate
Reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([N:16]=[N+:17]=[N-:18])[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[CH3:21].Cl[CH2:23]Cl.CO>C[Si](C=[N+]=[N-])(C)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([N:16]=[N+:17]=[N-:18])[C:13]([O:15][CH3:23])=[O:14])=[CH:4][C:3]=1[CH3:21]Participants
4
Procedure
To a solution of crude (R)-6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoic acid (0.163 g, 0.552 mmol) in 10 mL of dichloromethane/methanol (4:1), trimethylsilyldiazomethane was added dropwise until the solution became yellow. After stirred at room temperature under N2 for 30 min, the reaction mixture was concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-100% dichloromethane/hexanes to give the title compound as colorless oil (0.141 g, 83% yield)