Tetrahydrofuran → HCID 67536727, compound

HRID 2383037Notes

Reaction equation

HRID 2383037 reaction equation
[C:1]([Li])([CH3:4])(C)[CH3:2].[CH3:6][C:7]([CH3:21])([CH3:20])[C:8]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11]1)=[O:9].CN(C)CCN(C)C.C1C[O:33]CC1>CCCCC.C(O)(=O)C.CC(C)=O>[CH3:6][C:7]([CH3:21])([CH3:20])[C:8]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]1[C:1]([OH:33])([CH3:4])[CH3:2])=[O:9]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 5197459HCID 5197459, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 67536727HCID 67536727, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1.64 M tert-butyllithium in n-pentane (12 mL) was added to a mixture of 2-(2,2-dimethylpropanoyl)-1,2,3,4-tetrahydroisoquinoline (3.0 g), tetramethylethylenediamine (2.2 ml), and THF (40 mL) at −78° C. The reaction liquid was stirred at −78° C. for 10 minutes. Then, acetone (1.8 mL) was further added to the liquid at −78° C., followed by stirring at −78° C. for 1 hour. Acetic acid (2 mL) was added to the reaction liquid, and the temperature was raised to room temperature. The reaction liquid was evaporated under reduced pressure. EtOAc and water were added thereto, followed by liquid separation. The organic layer was washed sequentially with an aqueous 5% citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 2-[2-(2,2-dimethylpropanoyl)-1,2,3,4-tetrahydroisoquinolin-1-yl]propan-2-ol (2.62 g).

Workup

  1. customThe reaction liquid
  2. stirringby stirring at −78° C. for 1 hour
  3. temperaturethe temperature was raised to room temperature
  4. customThe reaction liquid
  5. customwas evaporated under reduced pressure
  6. additionEtOAc and water were added
  7. customfollowed by liquid separation
  8. washThe organic layer was washed sequentially with an aqueous 5% citric acid solution
  9. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over magnesium sulfate
  10. customevaporated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-e0c5458bfb37463c9fa7a5c851434377
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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