Tetrahydrofuran → N-[(1R)-1-(6-methylpyridin-3-yl)ethyl]-2-methylpropane-2-sulfinamide
Reaction equation
C1COCC1.[CH3:6][C:7]1[N:12]=[CH:11][C:10]([C:13](=O)[CH3:14])=[CH:9][CH:8]=1.[CH3:16][C:17]([S@:20]([NH-:22])=[O:21])([CH3:19])[CH3:18].[BH4-].[Na+]>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC.CCO.O>[CH3:6][C:7]1[N:12]=[CH:11][C:10]([C@H:13]([NH:22][S:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21])[CH3:14])=[CH:9][CH:8]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
To a THF (25 ml) solution of 1-(6-methylpyridin-3-yl)ethanone (2.1 g, 15.5 mmol), (R)-(+)-2-methyl-2-propanesulfinylamide (2.26 g, 18.6 mmol) and titanium(IV) ethoxide (25 ml) were added and the mixture was stirred for 24 hours at 70° C. Then, the mixture was cooled to 0° C. and sodium borohydride (2060 mg, 54 mmol) was added. After stirring for 2 hours, water and EtOH were added to the mixture with stirring for 1 hour at room temperature. Filtration, evaporation gave N-[(1R)-1-(6-methylpyridin-3-yl)ethyl]-2-methylpropane-2-sulfinamide which was treated with hydrochloric acid-MeOH (2.0 M, 15.0 ml) and 1,4-dioxane (15.0 ml) for 1.5 hours at room temperature. Then, the reaction mixture was evaporated and diethyl ether was added to form a precipitate, which was collected, washed with diethyl ether to give (1R)-1-(6-methylpyridin-3-yl)ethanamine hydrochloride (2.12 g, 28%). MS (ESI) m/z 161 (M−H)−.
Workup
- temperatureThen, the mixture was cooled to 0° C.
- stirringAfter stirring for 2 hours
- stirringwith stirring for 1 hour at room temperature
- filtrationFiltration, evaporation
Sources & evidence
- ORD record
- ord-471d17682966413d9d1dd1e854bd74fb
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178558B2
Reaction notes
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