Aluminium lithium hydride → 2-(4-Aminomethyl-3-fluoro-phenyl)-propan-2-ol

HRID 2181691Notes

Reaction equation

HRID 2181691 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([C:10]([OH:13])([CH3:11])[CH3:12])=[CH:9][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 224816262-Fluoro-4-(2-hydroxypropan-2-yl)benzonitrile

Product 1

HCID 224816482-(4-Aminomethyl-3-fluoro-phenyl)-propan-2-olYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.95 g (0.011 mol) 2-fluoro-4-(1-hydroxy-1-methyl-ethyl)-benzonitrile in 30 mL anhydrous THF at 0° C. was added dropwise 34 mL (0.034 mol) 1.0M LiAlH4. The mixture was warmed to room temperature then heated to reflux for 30 minutes. The mixture was then cooled to 0° C. and quenched with 20 mL MeOH added dropwise. Next, it was diluted with 700 mL CHCl3 and washed with 100 mL water. The resulting suspension was filtered through Celite and the organic layer dried over MgSO4 and concentrated to give 1.6 g of an amber oil.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 30 minutes
  3. temperatureThe mixture was then cooled to 0° C.
  4. customquenched with 20 mL MeOH
  5. additionadded dropwise
  6. additionNext, it was diluted with 700 mL CHCl3
  7. washwashed with 100 mL water
  8. filtrationThe resulting suspension was filtered through Celite
  9. dry with materialthe organic layer dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c58fd6e65a664af59bf5fb5a4657bfe9
Source dataset
uspto-grants-2005_05
Patent number
US06894041B2

Reaction notes

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