Tetrahydrofuran → (2R,5S)-1-benzyl-2,5-dimethylpiperazine

HRID 1838239ノート

反応式

HRID 1838239 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[CH2:12]([N:19]1[C@H:24]([CH3:25])[C:23](=O)[NH:22][C@@H:21]([CH3:27])[C:20]1=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH2:12]([N:19]1[CH2:20][C@H:21]([CH3:27])[NH:22][CH2:23][C@H:24]1[CH3:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11673088(3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dioneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 10632028(2R,5S)-1-benzyl-2,5-dimethylpiperazine収率 85.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

In an atmosphere of argon, 0.57 g of lithium aluminum hydride was added at 0° C. to 30 ml of THF solution containing 1.0 g of (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione, and the mixture was stirred overnight with heating under reflux. The reaction mixture was cooled to 0° C., 1.0 ml of water was added dropwise thereto and 1.0 ml of 10% aqueous sodium hydroxide was added dropwise thereto, and then the mixture was further mixed with 1.0 ml of water and stirred for 30 minutes. The precipitate was separated by filtration and washed with ethyl acetate, and the filtrate was washed with 10% aqueous potassium carbonate and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated. The residue was subjected to a silica gel column chromatography and eluted with chloroform-methanol-28% aqueous ammonia (25:1:0.1, v/v/v) to obtain 0.75 g of the title compound as a yellow oily substance.

後処理

  1. temperaturewith heating
  2. temperatureunder reflux
  3. stirringstirred for 30 minutes
  4. customThe precipitate was separated by filtration
  5. washwashed with ethyl acetate
  6. washthe filtrate was washed with 10% aqueous potassium carbonate and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washeluted with chloroform-methanol-28% aqueous ammonia (25:1:0.1, v/v/v)

出典と根拠

ORDレコード
ord-82e08a76750a4893b775c813a58a4ed4
出典データセット
uspto-grants-2004_01
特許番号
US06673799B1

反応ノート

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