Aluminium lithium hydride → (betaR,gammaR)-gamma-ethyl-N,N,beta-trimethyl-3-(phenylmethoxy)benzenepropanamine

HRID 1771009Notes

Reaction equation

HRID 1771009 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]>O1CCCC1>[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

4

Reactant 2

HCID 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 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum tetrahydride (730 mg, 20 mmol) was suspended in tetrahydrofuran (10 ml), then it was cooled in an ice-water bath and the solution of product of Example 5 (3 g, 9.2 mmol) in tetrahydrofuran (10 ml) was added dropwise. The reaction was carried out for 2 hours and quenched by adding 10% NaOH aqueous solution, Then the reaction solution was extracted with ethyl acetate for three times, and the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a pale yellow oil 2.7 g, yield: 93%. 1HNMR (300 MHz, CDCl3): δ 7.3-7.5 (5H, m), 7.2 (1H, t, J=7.6, 15.1), 6.8 (1H, d, J=8.5), 6.7 (2H, m), 5.0 (2H, s), 2.2-2.3 (2H, m), 2.2 (3H, s), 2.1 (3H, s), 1.8-1.9 (1H, m), 1.7-1.8 (1H, m), 1.5-1.6 (1H, m), 1.4-1.5 (1H, m), 1.0 (3H, d, J=6.2), 0.8 (3H, t, J=7.4, 14.7). ESI-MS: 312.3 (M+H).

Workup

  1. temperatureit was cooled in an ice-water bath
  2. customquenched
  3. additionby adding 10% NaOH aqueous solution
  4. extractionthe reaction solution was extracted with ethyl acetate for three times
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8a512af0c13e471698edad296929a343
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

Loading…