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Water → 1-[6-(N-tert-Butoxycarbonylamino)-1-hexyl]-1,2,3,4-tetrahydroquinoline-2-one

HRID 555325
ノート
印刷プレビュー

反応式

HRID 555325 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[O:11]=[C:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1.[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)=[O:28])([CH3:25])([CH3:24])[CH3:23].O>C1(C)C=CC=CC=1.O1CCCC1>[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][C:12]1=[O:11])=[O:28])([CH3:25])([CH3:24])[CH3:23]
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 962WaterHCID 64796HydrocarbostyrilHCID 3251421Potassium bis(trimethylsilyl)amideHCID 16211353tert-Butyl (6-bromohexyl)carbamate

生成物 1

HCID 669882961-[6-(N-tert-Butoxycarbonylamino)-1-hexyl]-1,2,3,4-tetrahydroquinoline-2-one

試薬・触媒・溶媒 2

HCID 1140Toluene
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

0.5M Potassium bis-(trimethylsilyl)-amide in toluene (10 ml) was added dropwise at −30° C. in an argon atmosphere to a stirred solution of 2-oxo-1,2,3,4-tetrahydroquinoline (735 mg) in tetrahydrofuran (50 ml). After further cooling to −50° C. a solution of N-(tert-butoxycarbonyl)-6-bromo-hexylamine (1.5 g) in tetrahydrofuran (10 ml) was added slowly. Subsequently the temperature was allowed to raise to room temperature followed by heating at 50-60° C. for 48 hours. Ice and water were added and the mixture was extracted twice with ethyl acetate. The organic phases were washed with saturated sodium chloride, dried and evaporated to leave a yellow oil which after purification by chromatography on silica gel with ethyl acetate/hexane (1:1) as eluent gave the desired compound as a colourless oil.

後処理

  1. additionwas added slowly
  2. temperatureby heating at 50-60° C. for 48 hours
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe organic phases were washed with saturated sodium chloride
  5. customdried
  6. customevaporated
  7. customto leave a yellow oil which
  8. customafter purification by chromatography on silica gel with ethyl acetate/hexane (1:1) as eluent

出典と根拠

ORDレコード
ord-755de4918fee4d9aa5ce21b2aa2929dd
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08053446B2

反応ノート

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