Formic Acid → 2-(4-Bromophenyl)-1-methylpyrrolidine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[CH:13](O)=O.C=O>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][CH2:10][N:9]2[CH3:13])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 2-(4-bromophenyl)pyrrolidine (0.5 g, 2.2 mmol), formic acid (0.11 mL, 2.42 mmol), formaldehyde (0.2 mL, 2.42 mmol, 37% in water), water (4 mL) in a sealed tube was heated to 150° C. under microwave for 5 minutes. After cooling to room temperature the reaction mixture was extracted with EtOAc (3×15 mL), the combined organic phase was washed consecutively with saturated NaHCO3 (5 mL) and brine (5 mL), dried over Na2SO4 and concentrated in vacuo to give the crude product (0.48 g, 91%), which was used directly in the next step. LC-MS (ESI) m/z: 240 (M+1)+.
Workup
- temperatureAfter cooling to room temperature the reaction mixture
- extractionwas extracted with EtOAc (3×15 mL)
- washthe combined organic phase was washed consecutively with saturated NaHCO3 (5 mL) and brine (5 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-42d592dbd79b4d7dbac6b705f49074f3
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420650B2
Reaction notes
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