Borane;tetrahydrofuran → [(3-Bromo-4-fluorophenyl)methyl](methyl)amine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:11](=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[F:8].B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]Participants
4
Conditions
- Temperature
- 8 °C
Procedure
To the solution of 1,1-dimethylethyl [(3-bromo-4-fluorophenyl)methyl]carbamate (0.755 g, 2.48 mmol) in THF (1 mL) was added BH3.THF (12.5 mL, 1.0 M in THF). The mixture was heated in a microwave machine at about 8° C. for about 30 mins twice. The reaction was then quenched with HCl (10 mL, 1 N) slowly, stirred for 2 h at room temperature, basified with NaHCO3 to pH ˜9, and extracted with EtOAc (50+20 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated to afford 0.52 g (96%) of the title compound. LC-MS m/z 218 (M+H)+.
Workup
- customThe reaction was then quenched with HCl (10 mL, 1 N) slowly
- extractionextracted with EtOAc (50+20 mL)
- washThe organic layer was washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6e4731a5970b4eb5ac91fd740abca36c
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084449B2
Reaction notes
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