Aluminum → (betaR,gammaR)-gamma-ethyl-N,N,beta-trimethyl-3-(phenylmethoxy)benzenepropanamine

HRID 1771016Notes

Reaction equation

HRID 1771016 reaction equation
[H-].[H-].[H-].[H-].[Al+3].[Li+].[CH2:7]([C@@H:9]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1)[C@@H:10]([CH3:16])[C:11]([N:13]([CH3:15])[CH3:14])=O)[CH3:8].[Al]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:7]([C@@H:9]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:18]=1)[C@@H:10]([CH3:16])[CH2:11][N:13]([CH3:15])[CH3:14])[CH3:8]

Participants

6

Reactant 3

HCID 5359268AluminumHCID 21226445Aluminium lithium hydrideHCID 60164737(alphaR,betaR)-beta-ethyl-N,N,alpha-trimethyl-3-(phenylmethoxy)benzenepropanamide

Product 1

HCID 60164845(betaR,gammaR)-gamma-ethyl-N,N,beta-trimethyl-3-(phenylmethoxy)benzenepropanamineYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum tetrahydride (730 mg, 20 mmol) was suspended in tetrahydrofuran (10 ml), the product of Example 5 (3.2 g, 10 mmol) was dissolved in toluene, cooled in an ice-water bath, the solution of red aluminum in toluene (9 mL, 30 mmol) was added dropwise, the reaction was carried out for 2 hours and then quenched by adding 10% NaOH aqueous solution. After the reaction solution was separated, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give a pale yellow oil 2.8 g, yield: 90%. The HNMR spectrum data is the same as that in Example 6.

Workup

  1. temperaturecooled in an ice-water bath
  2. customquenched
  3. additionby adding 10% NaOH aqueous solution
  4. customAfter the reaction solution was separated
  5. washthe organic phase was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f5077149cbb74c7d956aa00e45121a29
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

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