HCID 19775331, compound → HCID 19775326, compound

HRID 1613181Notes

Reaction equation

HRID 1613181 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:10]1[CH:37]=[CH:36][C:13]([CH2:14][CH2:15][N:16]([C:18]([CH3:35])([CH3:34])[CH2:19][O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:17])=[CH:12][CH:11]=1)(=O)[NH2:8]>O1CCCC1>[NH2:8][CH2:7][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][CH2:15][N:16]([C:18]([CH3:35])([CH3:34])[CH2:19][O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH3:17])=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 19775331HCID 19775331, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19775326HCID 19775326, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (57 mg) was added to a solution of 2-[N-(4-carbamoylphenethyl)-N-methylamino]-1-diphenylmethoxy-2-methylpropane (170 mg -- see Example 42) in tetrahydrofuran (12 ml) and the mixture was stirred at room temperature for 17 hours, heated under reflux for 2 hours, quenched by the sequential dropwise addition with stirring of a solution of water (57 mg) in tetrahydrofuran (1 ml), 15% aqueous sodium hydroxide solution (57 mg) and water (156 mg), stirred at room temperature for 30 minutes and filtered. The filtrate was evaporated and the residue was partitioned between methylene chloride and 5% aqueous sodium carbonate solution. The organic layer was washed with water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (17 g) using hexane:ether:diethylamine (90:5:5) as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless oil (86 mg, 52%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customquenched by the sequential dropwise addition
  4. stirringwith stirring of a solution of water (57 mg) in tetrahydrofuran (1 ml), 15% aqueous sodium hydroxide solution (57 mg) and water (156 mg)
  5. stirringstirred at room temperature for 30 minutes
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customthe residue was partitioned between methylene chloride and 5% aqueous sodium carbonate solution
  9. washThe organic layer was washed with water
  10. dry with materialdried over magnesium sulphate
  11. customevaporated
  12. customThe residue was purified by chromatography on silica (17 g)
  13. customevaporated

Sources & evidence

ORD record
ord-3ca0161a856943c18ced3729ee8dcc18
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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