Triphenylphosphine → tert-butyl {(1S)-2-[(6-bromopyridin-3-yl)oxy]-1-methylethyl}carbamate
Reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.O[CH2:10][C@@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:12][C@@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH3:10])=[CH:4][CH:3]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 6-bromopyridin-3-ol (4.90 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (4.93 g) and triphenylphosphine (11.06 g) in THF (100 mL) was added dropwise a toluene solution (1.9 M, 22 mL) of diisopropyl azodicarboxylate, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed with water and saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (5.35 g).
Workup
- washthe mixture was washed with water and saturated aqueous sodium hydrogen carbonate solution
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-fb98801dd30d45f6a813feebea152a43
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729102B2
Reaction notes
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