Aluminium lithium hydride → (R)-4-Benzyl-3-methylmorpholine
Reaction equation
[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][O:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][O:11][CH2:12][C@H:13]1[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (R)-4-benzyl-5-methylmorpholine-3-one (3.0 g, 14.22 mmol) in THF (10 mL) was added dropwise at 0° C. to a solution of lithium aluminum hydride (1.0 M solution in THF, 28.5 mL, 28.5 mmol) in THF (10 mL). The ice bath was removed and the reaction mixture was heated at reflux for 18 h. The reaction was cooled in an ice-bath and excess hydride reagent was quenched by careful, dropwise addition of H2O (5 mL), 15% sodium hydroxide (5 mL) and H2O (15 mL). The resulting mixture was stirred at room temperature for 1 h and the reaction mixture was filtered through a pad of Celite and the pad rinsed with EtOAc (100 mL). The filtrate was washed with saturated brine solution, dried (Na2SO4), filtered and concentrated under reduced pressure to provide (R)-4-benzyl-3-methylmorpholine (2.66 g, 95%) as a red oil. 1H NMR and MS consistent.