Sodium Hydroxide → 2-(R)-[2-(N,N-Dimethylamino)ethyl]-6-(4-hydroxyphenyl) methoxytetralin

HRID 1242889Notes

Reaction equation

HRID 1242889 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][C@@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24]C(C4C=CC(OC)=CC=4)=O)=[CH:20][CH:19]=3)[CH:12]=2)[CH2:7]1)[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[CH3:1][N:2]([CH2:4][CH2:5][C@@H:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=3)[CH:12]=2)[CH2:7]1)[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 587151182-(R)-[2-(N,N-Dimethylamino)ethy]-6-(4-[(4-methoxyphenyl)carbonyloxy]benzyloxy)tetralin

Product 1

HCID 587151162-(R)-[2-(N,N-Dimethylamino)ethyl]-6-(4-hydroxyphenyl) methoxytetralinYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

THF solution (2 ml) of 2-(R)-[2-(N,N-dimethylamino)ethyl]-6-[4-(4-methoxyphenylcarbonyloxy) phenylmethoxy]tetralin (330 mg) was added dropwise to THF suspension (4 ml) of lithium aluminum hydride (60 mg) under ice-cooling. 1N aqueous sodium hydroxide solution was added the reaction mixture to make the mixture basic, and the precipitate was removed by celite filtration. After the filtrate was concentrated, the residue was purified using silica gel chromatography (development solvent; ethyl acetate-methanol), and recrystallized (ethyl acetate-hexane) to give the titled compound (70 mg).

Workup

  1. temperaturecooling
  2. customthe precipitate was removed by celite filtration
  3. concentrationAfter the filtrate was concentrated
  4. customthe residue was purified
  5. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-a7715b6530354a0c9673e8e4096830f1
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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