Sodium hydride → (5S)-4-[(4-Methoxyphenyl)methyl]-5-methylmorpholin-3-one

HRID 385766ノート

反応式

HRID 385766 の反応式
[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]=1

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 67041745HCID 67041745、化合物

生成物 1

HCID 15225767(5S)-4-[(4-Methoxyphenyl)methyl]-5-methylmorpholin-3-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
25 °C

実験手順

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.

後処理

  1. customInto a 10000 mL 4-necked, round bottomed flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customUpon completion, the reaction mixture was quenched
  4. additionby adding 1000 mL of ethanol and 250 mL of water
  5. additionThe resulting solution was further diluted with 1500 mL of dichloromethane
  6. washwashed three times with 2000 mL of water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-af6cdb33c6394e4ea05c9e88260b7281
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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