Water → 2-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-2-methylpropan-1-ol

HRID 1807035Notes

Reaction equation

HRID 1807035 reaction equation
C([O:3][C:4](=O)[C:5]([C:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH:13]=1)([CH3:7])[CH3:6])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[CH2:14]([N:11]1[CH2:10][CH:9]=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][OH:3])[CH2:13][CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 545483681-Phenylmethyl-alpha,alpha-dimethyl-1,2,3,6-tetrahydro-4-pyridine-acetic acid ethyl ester

Product 1

HCID 672968432-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-2-methylpropan-1-olYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step C To a solution of 2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-methyl-propionic acid ethyl ester (6 g, 21 mmol) in anhydrous tetrahydrofuran 75 mL) at 0° C. was added a tetrhydrofuran solution (1 M) of LiAlH4 (84 mL, 84 mmol) under nitrogen. The reaction mixture was heated at reflux for 3 h, then cooled to room temperature. Water and aqueous NaOH solution (2N) was added. The mixture was filtered to remove the precipitate, and the filtrate was concentrated. Water was added, and the mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 2-(1-benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2-methyl-propan-1-ol as a brown oil (4.73 g, 77%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. filtrationThe mixture was filtered
  4. customto remove the precipitate
  5. concentrationthe filtrate was concentrated
  6. additionWater was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. customThe organic layer were separated
  9. washwashed with water, aqueous HCl solution, brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7ed188419c0f4c839cd16e2ac0a9c891
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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