Triphenylphosphine → HCID 67202457, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:30]([O:34][C:35]([N:37]1[CH2:42][CH2:41][CH:40]([OH:43])[CH2:39][CH2:38]1)=[O:36])([CH3:33])([CH3:32])[CH3:31].CC(OC(/N=N/C(OC(C)C)=O)=O)C>CCOC(C)=O.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1)[O:43][CH:40]1[CH2:41][CH2:42][N:37]([C:35]([O:34][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:36])[CH2:38][CH2:39]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
3-Bromo-5-methoxyphenol (0.18 g, 0.89 mmol) and triphenylphosphine (0.284, 1.07 mmol) were taken into THF (5 mL) and the resulting mixture cooled to 0° C. 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.18 g, 0.89 mmol), and DIAD (0.207 mL, 1.07 mmol) were taken up into THF (5 mL) and added slowly to the mixture, which was then stirred at room temperature over night. The resulting mixture was taken into EtOAc and washed with saturated NaHCO3 and brine. The solvent was dried over sodium sulfate and removed in vacuo. The resulting residue was purified on normal phase chromatography (EtOAc/heptane) to yield tert-butyl 4-(3-bromo-5-methoxyphenoxy)piperidine-1-carboxylate. MH+ 386.2, 388.2
Workup
- additionadded slowly to the mixture, which
- washwashed with saturated NaHCO3 and brine
- dry with materialThe solvent was dried over sodium sulfate
- customremoved in vacuo
- customThe resulting residue was purified on normal phase chromatography (EtOAc/heptane)
Sources & evidence
- ORD record
- ord-f689a246f02842ffa248aaf5e98ce31a
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633322B2
Reaction notes
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