HCID 13281980, compound → (4aR,8aS)-2-Methyl-4a-phenyldecahydroisoquinoline

HRID 26472Notes

Reaction equation

HRID 26472 reaction equation
[CH3:1][N:2]1[C:11](=O)[CH2:10][C@@:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]1[CH2:11][CH2:10][C@@:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3]1

Participants

4

Reactant 2

HCID 13281980HCID 13281980, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15577119(4aR,8aS)-2-Methyl-4a-phenyldecahydroisoquinolineYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methyl-4a-phenyl-1,3-diketo-cis-decahydroisoquinoline (1.9 g) in 75 ml of anhydrous tetrahydrofuran was treated with lithium aluminum hydride (2.0 g) and refluxed overnight. The reaction was quenched by the successive addition of 2.0 ml of water, 2.0 ml of 15% sodium hydroxide and finally 6.0 ml of water. The inorganic salts were filtered and washed well with ether. The combined filtrates were evaporated to yield 1.6 g of an oil which was evaporatively distilled, bp 125° (0.05 mm), nD20 1.5514, and identified as N-methyl-4a-phenyl-cis-decahydroisoquinoline.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction was quenched by the successive addition of 2.0 ml of water, 2.0 ml of 15% sodium hydroxide and finally 6.0 ml of water
  3. filtrationThe inorganic salts were filtered
  4. washwashed well with ether
  5. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-683027f302cb427296b30eb7968c395b
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

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