HCID 19775303, compound → HCID 19775318, compound

HRID 1613177Notes

Reaction equation

HRID 1613177 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:14][CH2:15][C:16]([N:19]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](OC)=[O:30])=[CH:25][CH:24]=2)[CH3:20])([CH3:18])[CH3:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[C:33]1([CH:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:14][CH2:15][C:16]([N:19]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([CH2:29][OH:30])=[CH:27][CH:28]=2)[CH3:20])([CH3:17])[CH3:18])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 19775303HCID 19775303, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19775318HCID 19775318, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (38 mg) was added to a stirred, ice-cooled solution of 1-diphenylmethoxy-2-[N-(4-methoxycarbonylphenethyl)-N-methylamino]-2-methylpropane (160 mg) (see Example 13) in ether (15 ml) and the mixture was stirred at room temperature for 17 hours, heated under reflux for 4 hours, quenched by the sequential dropwise addition with stirring of a solution of water (38 mg) in tetrahydrofuran (2 ml), 15% aqueous sodium hydroxide solution (38 mg) and water (114 mg), stirred at room temperature for 30 minutes and filtered. The filtrate was washed with 5% aqueous sodium carbonate solution and water, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica (17 g) using hexane:n-propanol: saturated methanolic ammonia (95:5:1) as the eluant. Appropriate fractions were combined and evaporated to give the title compound as a colourless oil (130 mg, 87%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. customquenched by the sequential dropwise addition
  4. stirringwith stirring of a solution of water (38 mg) in tetrahydrofuran (2 ml), 15% aqueous sodium hydroxide solution (38 mg) and water (114 mg)
  5. stirringstirred at room temperature for 30 minutes
  6. filtrationfiltered
  7. washThe filtrate was washed with 5% aqueous sodium carbonate solution and water
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue was purified by chromatography on silica (17 g)
  11. customevaporated

Sources & evidence

ORD record
ord-247207dc5ab44ed7a549854abd8fe0da
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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