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

HRID 555325
Notes
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Reaction equation

HRID 555325 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 64796HydrocarbostyrilHCID 3251421Potassium bis(trimethylsilyl)amideHCID 16211353tert-Butyl (6-bromohexyl)carbamate

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-755de4918fee4d9aa5ce21b2aa2929dd
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08053446B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes