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Triethylsilane → HCID 58340820, compound

HRID 1258872
Notes
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Reaction equation

HRID 1258872 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([C:20]3[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=3[CH:27]([CH3:29])[CH3:28])O)[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC.OS(C(F)(F)F)(=O)=O>C(O)(C(F)(F)F)=O>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][C:20]3[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:21]=3[CH:27]([CH3:29])[CH3:28])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 67115832HCID 67115832, compound

Product 1

HCID 58340820HCID 58340820, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (1-benzyl-1,2,3,4-tetrahydro-quinolin-7-yl)-(5-bromo-2-isopropyl-phenyl)-methanol (2.61 g, 5.79 mmol) in TFA (7.0 mL), Et3SiH (4.63 mL, 28.95 mmol) was added followed by triflic acid (1.0 mL, 11.5 mmol) at room temperature. The reaction mixture was stirred at room temperature for 30 min. The reaction was evaporated to dryness and neutralized by adding saturated aqueous NaHCO3 (15 mL). The resulting mixture was extraction with dichloromethane (3×30 mL). Crude product obtained after evaporation solvent was purified by using neutral alumina column chromatography to furnish 1-benzyl-7-(5-bromo-2-isopropyl-benzyl)-1,2,3,4-tetrahydro-quinoline (1.80 g).

Workup

  1. customThe reaction was evaporated to dryness
  2. additionby adding saturated aqueous NaHCO3 (15 mL)
  3. extractionextraction with dichloromethane (3×30 mL)
  4. customCrude product obtained
  5. customafter evaporation solvent
  6. customwas purified

Sources & evidence

ORD record
ord-497b4312fe894d339d5846f3ad86a2cb
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08466114B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes