Potassium Sodium Tartrate → HCID 59396634, compound

HRID 2383028Notes

Reaction equation

HRID 2383028 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:26])([F:25])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][N:16]=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[F:26][C:8]([F:7])([F:25])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][NH:16]1

Participants

6

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 67538453HCID 67538453, compound

Product 1

HCID 59396634HCID 59396634, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under cooling in a dry ice-acetone bath, lithium aluminum hydride (1.03 g) was added to THF (30 mL) to make a suspension. A solution of 1-[2-(trifluoromethyl)phenyl]-3,4-dihydroisoquinoline (6.22 g) in THF (30 mL) was added dropwise to the suspension under an argon atmosphere. The reaction solution was stirred at room temperature for 15 hours. The reaction liquid was cooled in ice and then a saturated aqueous Rochelle salt solution (1.5 mL) was added to stop the reaction. The liquid was stirred at room temperature for 1 hour and magnesium sulfate and celite were then added thereto. The mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 1-[2-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydroisoquinoline (5.42 g).

Workup

  1. temperatureUnder cooling in a dry ice-acetone bath
  2. customThe reaction liquid
  3. temperaturewas cooled in ice
  4. customthe reaction
  5. stirringThe liquid was stirred at room temperature for 1 hour
  6. filtrationThe mixture was filtered through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-43a4ae45214443659c2e10c100d6c5b1
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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