Sodium hydride → Tert-butyl 4-[(1-benzylpiperidin-3-yl)methyl]-3-oxopiperazine-1-carboxylate

HRID 603180ノート

反応式

HRID 603180 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CC1C=CC(S(O[CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][N:31]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:30]2)(=O)=O)=CC=1>CN(C)C=O>[CH2:35]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([CH2:28][N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]2=[O:14])[CH2:30]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

5

反応物 3

HCID 24758Sodium hydride3 回HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 57656889(1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

生成物 1

HCID 57656824Tert-butyl 4-[(1-benzylpiperidin-3-yl)methyl]-3-oxopiperazine-1-carboxylate収率 20%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of tert-butyl-3-oxopiperazine-1-carboxylate (250 mg) in dimethylformamide (10 mL) was added sodium hydride (55 mg) at room temperature under argon. The mixture was stirred at room temperature 15 minutes before a solution of (1-benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate (492 mg) in dimethylformamide (5 mL) was added. The mixture was stirred overnight at room temperature before sodium hydride (60 mg) was added and the mixture was stirred for 48 hours. A further quantity of sodium hydride (60 mg) was added and the mixture was stirred for 5 hours and then quenched by the addition of water. The mixture was then partitioned between water and ethyl acetate. The layers were separated and the organic layer washed twice with water and once with brine. The organic layer was then dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 70% ethyl acetate in hexane to give the title compound as a colourless oil (95 mg, 20%).

後処理

  1. additionwas added
  2. additionwas added
  3. stirringthe mixture was stirred for 5 hours
  4. customquenched by the addition of water
  5. customThe mixture was then partitioned between water and ethyl acetate
  6. customThe layers were separated
  7. washthe organic layer washed twice with water and once with brine
  8. dry with materialThe organic layer was then dried over sodium sulfate
  9. customevaporated
  10. customThe residue was purified by silica column chromatography
  11. washeluting with a gradient of 0 to 70% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-58bcac76c8e14fb88b034749188408d9
出典データセット
uspto-grants-2011_03
特許番号
US07906645B2

反応ノート

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