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Sodium Hydroxide → 1-Benzyl-3-(1-tert-butoxycarbonylaminocyclobutyl)pyrrolidine

HRID 1457991
ノート
印刷プレビュー

反応式

HRID 1457991 の反応式
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2([NH2:17])[CH2:16][CH2:15][CH2:14]2)[CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[C:27]([O:31][C:32](=O)[O:33]C(C)(C)C)([CH3:30])([CH3:29])[CH3:28]>O1CCCC1.O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:13]2([NH:17][C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])[CH2:16][CH2:15][CH2:14]2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 21226445Aluminium lithium hydrideHCID 221005151-Benzyl-4-(1-aminocyclobutyl)-2-pyrrolidone

生成物 1

HCID 221004971-Benzyl-3-(1-tert-butoxycarbonylaminocyclobutyl)pyrrolidine収率 26%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
2 回
HCID 8028Tetrahydrofuran溶媒

実験手順

A 1.50 g (6.14 mmol) portion of 1-benzyl-4-(1-aminocyclobutyl)-2-pyrrolidone (fr. 2) was dissolved in 200.0 ml of tetrahydrofuran to which, with cooling in an ice bath, was subsequently added 932 mg (24.56 mmol) of lithium aluminum hydride in small portions. After 12 hours of stirring with heating under reflux, the reaction solution was cooled in an ice bath and mixed with 932 μl of water in small portions, 932 μl of 15% sodium hydroxide aqueous solution and 932 μl of water in that order. After 30 minutes of stirring at room temperature, insoluble material was removed by filtration and the solvent was evaporated. To the thus obtained syrup were added 70.0 ml of acetonitrile and then 1.69 ml (7.37 mmol) of di-tert-butylcarbonate at room temperature, followed by overnight stirring. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (230-400 mesh silica gel 150 ml, 5% methanol-chloroform) to yield 525 mg (26%) of the title compound.

後処理

  1. temperaturewith cooling in an ice bath
  2. temperaturewith heating
  3. temperatureunder reflux
  4. temperaturethe reaction solution was cooled in an ice bath
  5. stirringAfter 30 minutes of stirring at room temperature
  6. custominsoluble material was removed by filtration
  7. customthe solvent was evaporated
  8. additionTo the thus obtained syrup were added 70.0 ml of acetonitrile
  9. stirringstirring
  10. customAfter evaporation of the solvent
  11. customthe resulting residue was purified by a silica gel column chromatography (230-400 mesh silica gel 150 ml, 5% methanol-chloroform)

出典と根拠

ORDレコード
ord-445d913e6127454098cd470c102198a0
出典データセット
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05849757

反応ノート

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