Aluminium lithium hydride → HCID 178484123, compound

HRID 967164Notes

Reaction equation

HRID 967164 reaction equation
[CH3:1][NH:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)(=O)C>[CH2:17]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C@H:8]1[CH2:7][CH2:6][C@H:5]([CH2:3][NH:2][CH3:1])[CH2:10][CH2:9]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178485740HCID 178485740, compound

Product 1

HCID 178484123HCID 178484123, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

2.2 g (6.88 mmol) trans-4-(4-benzyloxy-butoxy)-cyclohexanecarboxylic acid methylamide dissolved in 10 ml of tetrahydrofuran were added slowly to a suspension of 0.261 g of lithium aluminium hydride in 10 ml of tetrahydrofuran. The reaction mixture was then stirred at 50° C. for 2 hours, cooled to 0° C., treated with 2 g of ice, stirred at room temperature for 30 minutes, diluted with ethyl acetate, dried over sodium sulfate, filtered and evaporated to give 2.05 g (97.4%) trans-[4-(4-benzyloxy-butoxy)-cyclohexylmethyl]-methyl-amine as light brown viscous oil, MS: 306 (MH+).

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred at room temperature for 30 minutes
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d81a941cb7a74268adaffb4183be97bc
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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