Boron tribromide → (R)-3-(1-Aminoethyl)phenol
Reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C@H:9]([NH2:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:11][C@@H:9]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1)[CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To the solution of (R)-1-(3-Methoxy-phenyl)-ethylamine (0.5 g, 3.31 mmol) in DCM (25 mL) at −78° C. was added 1.0M BBr3 solution in DCM (6.6 mL, 6.62 mmol) dropwise. The solution was warmed to room temperature and the reaction mixture was quenched with methanol (100 mL) and then concentrated in vacuo. This process was repeated until no white fumes were observed upon addition of methanol to afford 3-((R)-1-Amino-ethyl)-phenol as a pale yellow oil (0.51 g) which was used in the next step without further purification.
Workup
- customthe reaction mixture was quenched with methanol (100 mL)
- concentrationconcentrated in vacuo
- additionwere observed upon addition of methanol
Sources & evidence
- ORD record
- ord-b8976e43bd384dcda29050a7922d5460
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716473B2
Reaction notes
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