Tetrahydrofuran → N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine
Reaction equation
[CH3:1][N:2]([CH3:18])[C:3]([CH:5]1[CH2:9][C:8](=O)[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=O.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:1][N:2]([CH3:18])[CH2:3][CH:5]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.91 g (11.8 mmol) N,N-dimethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide and 15 ml anhydrous tetrahydrofuran was dropped into a suspension of 1.41 g (35 mmol) lithium aluminum hydride and 30 ml tetrahydrofuran The reaction was refluxed overnight then cooled to room temperature. To the solution was added 1.5 ml water, 1.5 ml 15% sodium hydroxide and 4.5 ml of water. The resulting precipitate was filtered The filtrate was concentrated under reduced pressure, dissolved in dichlromethane, dried over magnesium sulfate and the solvent evaporated under reduced pressure. The residue was bulb to bulb distilled giving 1.5 g (58%) of N,N-dimethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine as a clear liquid. This material was used in the next step.
Workup
- temperaturewas refluxed overnight
- filtrationThe resulting precipitate was filtered The filtrate
- concentrationwas concentrated under reduced pressure
- dissolutiondissolved in dichlromethane
- dry with materialdried over magnesium sulfate
- customthe solvent evaporated under reduced pressure
- distillationdistilled
Sources & evidence
- ORD record
- ord-07b657dcc08842b49fe57c83e8134a9a
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04638067
Reaction notes
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