Sodium Bicarbonate → [1-(4-Bromophenyl)-cyclopropyl]-propylamine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:11][C:12](=O)[CH2:13][CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:11][CH2:12][CH2:13][CH3:14])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
To a solution of N-[1-(4-bromophenyl)-cyclopropyl]-propionamide (Intermediate 11,7, 85.0 mg, 0.32 mmol) in THF (5 mL) at 0° C. was added BH3-Me2S (48.0 mg, 0.63 mmol; 0.31 mL of a 2M solution in THF). The solution was heated to 55° C. for 17 hours, cooled to room temperature, saturated aqueous NaHCO3 was added and the resulting mixture was stirred for 2 hours. This mixture was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound was isolated by column chromatography (10-30% EtOAc-hexanes).
Workup
- temperaturecooled to room temperature
- extractionThis mixture was extracted with EtOAc
- washthe combined organic layers were washed with H2O and saturated aqueous NaCl
- dry with materialbefore being dried (MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c08aef26d9304fe0a77bd9148ba09db3
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380256B1
Reaction notes
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