Benzyl Bromide → 5-Benzyl-7-t-butoxycarbonylamino-4-oxo-7-methyl-5-azaspiro[2.4]heptane

HRID 1096558ノート

反応式

HRID 1096558 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1([CH3:17])[C:13]2([CH2:15][CH2:14]2)[C:12](=[O:16])[NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCCCCC>CN(C)C=O.C(OCC)(=O)C>[CH2:20]([N:11]1[CH2:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH3:17])[C:13]2([CH2:14][CH2:15]2)[C:12]1=[O:16])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 577586467-t-Butoxycarbonylamino-4-oxo-7-methyl-5-azaspiro[2.4]heptane

生成物 1

HCID 577586535-Benzyl-7-t-butoxycarbonylamino-4-oxo-7-methyl-5-azaspiro[2.4]heptane収率 89.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

7-t-Butoxycarbonylamino-4-oxo-7-methyl-5-azaspiro[2.4]heptane (42.63 g) was suspended in dimethylformamide (850 mL) under a nitrogen gas atmosphere, and the suspension was cooled with ice. To the suspension, 60% sodium hydride (6.93 g) was added, and the mixture was returned to room temperature. Subsequently, benzyl bromide (22.64 mL) was added to the reaction mixture, followed by stirring. After three hours, insoluble material was removed through filtration, and water was added to the filtrate. Ethyl acetate was further added thereto for extraction. The organic layer obtained through extraction was dried with sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure, to thereby yield an oily residue. The residue was subjected to silica gel chromatography (hexane:ethyl acetate), to thereby yield the title product as pale yellow oil (51.0 g, yield: 89.2%).

後処理

  1. temperaturethe suspension was cooled with ice
  2. customwas returned to room temperature
  3. custominsoluble material was removed through filtration, and water
  4. additionwas added to the filtrate
  5. additionEthyl acetate was further added
  6. extractionfor extraction
  7. customThe organic layer obtained through extraction
  8. dry with materialwas dried with sodium sulfate
  9. filtrationfollowed by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customto thereby yield an oily residue

出典と根拠

ORDレコード
ord-137728d3992145958b377ea6872f1d13
出典データセット
uspto-grants-2012_03
特許番号
US08138352B2

反応ノート

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