Methanol → (R)-beta-aminophenethyl alcohol

HRID 2184995Notes

Reaction equation

HRID 2184995 reaction equation
[BH4-].[Li+].C[Si](C)(C)Cl.[CH:8]1[CH:9]=[CH:10][C:11]([C@@H:14]([NH2:18])[C:15](O)=[O:16])=[CH:12][CH:13]=1.CO>C1COCC1>[NH2:18][C@H:14]([C:11]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1)[CH2:15][OH:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 70134Phenylglycine, D-HCID 4148881Lithium borohydride

Product 1

HCID 2724025(R)-beta-aminophenethyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 g (920 mmol) of lithium borohydride were dissolved in 420 ml of absolute THF. 233.5 ml (1.84 mol) of trimethylchlorosilane were added dropwise with stirring and 69.5 g (0.46 mol) of (R)-phenylglycine were then added in portions in the course of 4 hours. The reaction mixture was stirred overnight at room temperature. 690 ml of methanol were then added, and the mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was dissolved in 690 ml of 20% strength aqueous potassium hydroxide solution with stirring. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and concentrated in vacuo. Yield: 41.2 g (65.3%).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 690 ml of 20% strength aqueous potassium hydroxide solution
  5. stirringwith stirring
  6. extractionThe aqueous phase was extracted three times with ethyl acetate
  7. washThe combined organic phases were washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5da119340b1644978fbfd2040f3743dc
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

Loading…