Sodium Hydroxide → 1-Aminomethyl-1-hydroxy-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

HRID 982091Notes

Reaction equation

HRID 982091 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][C:8]2=[O:13].C[Si]([C:24]#[N:25])(C)C.[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C(OCC)C.O.C(#N)C>[NH2:25][CH2:24][C:8]1([OH:13])[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) ChlorideHCID 122124065-Methoxy-3-phenyl-1-tetraloneHCID 21226445Aluminium lithium hydride

Product 1

HCID 200690361-Aminomethyl-1-hydroxy-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthaleneYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolvent

Procedure

5-Methoxy-3-phenyl-1,2,3,4-tetrahydro-1-naphthalenone (1.9 g, 7.5 mmol), the product of Example 1, 3 mL of acetonitrile, 1.9 g (19 mmol) of trimethylsilylcyanide, commercially available from Aldrich Chemical Company, and 100 mg of aluminum chloride were mixed together and heated at reflux temperature for 2 h. The reaction mixture was cooled and concentrated. The residue was dissolved in 6 mL of diethyl ether and the ether solution was added dropwise to a solution of 0.62 g (16 mmol) of lithium aluminum hydride in 14 mL of diethyl ether. After the reaction mixture was heated at reflux temperature for 2 h, 0.6 mL of water was added dropwise, followed by 0.6 mL of 15% aqueous sodium hydroxide solution, followed by 1.8 mL of water. The reaction mixture was stirred until a granular precipitate formed. The solid was filtered and washed with 3×20 mL of methylene chloride. The filtrate was concentrated to give 2.0 g (95% yield) of the title compound as an oil; 1H NMR (d6-DMSO) δ 1.90 (t, 1H), 2.25 (dt, 1H), 2.65-2.85 (m, 2H), 2.95-3.25 (m, 3H), 3.78 (s, 3H), 6.85-7.05 (m, 3H), 7.2-7.5 (m, 5H).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 6 mL of diethyl ether
  6. temperatureAfter the reaction mixture was heated
  7. temperatureat reflux temperature for 2 h
  8. customformed
  9. filtrationThe solid was filtered
  10. washwashed with 3×20 mL of methylene chloride
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f2a214c0758d4967962c9016120ec2a0
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

Loading…