Water → 3-(N-Methylamino)-1-(2-thienyl)-1-propanol, (-)-
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][NH:8][C:9](=O)[CH2:10][C@H:11]([OH:17])[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][NH:8][CH2:9][CH2:10][C@@H:11]([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[OH:17]Participants
Procedure
350 ml of dry tetrahydrofuran are initially introduced together with 10 g of lithium aluminium hydride and heated to reflux. At the same time, a start is made in adding 17 g of N-methyl-(3S)-3-hydroxy-3-(2-thienyl)propanamide from Example 14, dissolved in 150 g of tetrahydrofuran, dropwise. After this dropwise addition is complete, the mixture is subsequently stirred overnight under reflux. The mixture is then cooled down to room temperature and 200 ml of water are carefully added dropwise. 135 ml of a 10% solution of sodium hydroxide were then added dropwise and the solution was filtered. The solvent was removed in vacuo. 370 ml of 1 N sodium hydroxide solution were added to the crude solution and the whole was extracted 3 times with in each case 370 ml of toluene. The organic phases are combined and the volatile constituents are removed in vacuo, thereby providing 76 g (84% purity, 70% of theory).
Workup
- temperatureheated to reflux
- additionAfter this dropwise addition
- temperatureunder reflux
- filtrationthe solution was filtered
- customThe solvent was removed in vacuo
- addition370 ml of 1 N sodium hydroxide solution were added to the crude solution
- extractionthe whole was extracted 3 times with in each case 370 ml of toluene
- customthe volatile constituents are removed in vacuo
- customproviding 76 g (84% purity, 70% of theory)
Sources & evidence
- ORD record
- ord-40ed04085ab84fe48f0d6577e66cfa1b
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553970B2
Reaction notes
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