Aluminium lithium hydride → 3(3-Methoxyphenyl)-N,N,2-trimethyl pentane-1-amine, (2R,3R)-

HRID 1771012Notes

Reaction equation

HRID 1771012 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][CH3:24])[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][CH3:24])[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 53303234(alphaR,betaR)-beta-ethyl-3-methoxy-N,N,alpha-trimethylbenzenepropanamide

Product 1

HCID 112533283(3-Methoxyphenyl)-N,N,2-trimethyl pentane-1-amine, (2R,3R)-Yield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum tetrahydride (730 mg, 20 mmol) was suspended in tetrahydrofuran (10 ml), after the mixture was cooled in an ice-water bath, the solution of product of Example 15 (2.2 g, 9.0 mmol) in tetrahydrofuran (10 ml) was added dropwise, then the reaction was carried out for 2 hours, and quenched by adding 10% NaOH aqueous solution, after the reaction solution was extracted with ethyl acetate for three times, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a pale yellow oil 1.9 g, yield: 90%. 1HNMR (300 MHz, CDCl3): δ 7.2 (1H, t, J=7.9, 15.6), 6.6-6.8 (3H, m), 3.7 (3H, 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=6.3), 0.8 (3H, t, J=7.4, 14.5). ESI-MS: 236.3 (M+H).

Workup

  1. temperatureafter the mixture was cooled in an ice-water bath
  2. customquenched
  3. additionby adding 10% NaOH aqueous solution
  4. extractionafter the 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-595f44369c284648ac467a380d0a3b7d
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

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