Sodium hydride → (5S)-4-[(4-Methoxyphenyl)methyl]-5-methylmorpholin-3-one
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]([CH:15]([CH3:18])[CH2:16][OH:17])[C:11](=[O:14])[CH2:12]Br)=[CH:7][CH:6]=1>C1COCC1>[CH3:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]2[C@@H:15]([CH3:18])[CH2:16][O:17][CH2:12][C:11]2=[O:14])=[CH:7][CH:6]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Into a 10000 mL 4-necked, round bottomed flask purged and maintained with an inert atmosphere of nitrogen was placed a suspension of sodium hydride (125.6 g, 3.14 mol, 60%) in THF (5000 mL) and cooled to 25° C., followed by the addition of a solution of N-(4-methoxybenzyl)-2-bromo-N-(1-hydroxypropan-2-yl)acetamide (498 g, 1.57 mol) in THF (500 mL) dropwise over 30 minutes at 25° C. The resulting solution was allowed to stir overnight at 25° C. Upon completion, the reaction mixture was quenched by adding 1000 mL of ethanol and 250 mL of water. The resulting solution was further diluted with 1500 mL of dichloromethane and then washed three times with 2000 mL of water. The organic layer was dried over magnesium sulfate, filtered, and concentrated under vacuum to afford the title compound as a yellow oil.
Workup
- customInto a 10000 mL 4-necked, round bottomed flask purged
- temperaturemaintained with an inert atmosphere of nitrogen
- customUpon completion, the reaction mixture was quenched
- additionby adding 1000 mL of ethanol and 250 mL of water
- additionThe resulting solution was further diluted with 1500 mL of dichloromethane
- washwashed three times with 2000 mL of water
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-af6cdb33c6394e4ea05c9e88260b7281
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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