Ethyl Acetate → 2-[(2-Hydroxy-1,1-dimethyl-ethyl)-(1-phenyl-ethoxy)-amino]-2-methyl-propan-1-ol

HRID 1593792Notes

Reaction equation

HRID 1593792 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:26])[C:13](=[O:14])[O:12][CH2:11][C:10]([CH3:16])([CH3:15])[N:9]1[O:17][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19].[NH4+].[Cl-].CCOC(C)=O>C1COCC1.O>[OH:14][CH2:13][C:8]([N:9]([O:17][CH:18]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:19])[C:10]([CH3:15])([CH3:16])[CH2:11][OH:12])([CH3:7])[CH3:26]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 18552193HCID 18552193, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 179680362-[(2-Hydroxy-1,1-dimethyl-ethyl)-(1-phenyl-ethoxy)-amino]-2-methyl-propan-1-olYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2.93 (75 mmol) LiAlH4 in THF (100 ml) is slowly added at 0-10° C. a solution of 13.9 g (50 mmol) of compound 101 in THF (50 ml). After complete addition, the suspension is heated to reflux and kept at this temperature for 5 h. The mixture is cooled in an ice-bath and saturated NH4Cl-solution (25 ml) is added carefully. EtOAc (500 ml) and water (100 ml) is added, the phases separated and the organic layer washed with water (100 ml) and brine (100 ml), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 13.2 g (94%) of the title compound as a white solid.

Workup

  1. additionAfter complete addition
  2. temperaturethe suspension is heated
  3. temperatureto reflux
  4. temperatureThe mixture is cooled in an ice-bath
  5. customthe phases separated
  6. washthe organic layer washed with water (100 ml) and brine (100 ml)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0eef3806830243cc8819ef5ee5b417dc
Source dataset
uspto-grants-2007_11
Patent number
US07297819B2

Reaction notes

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