Methanol → (R)-beta-aminophenethyl alcohol

HRID 1602086Notes

Reaction equation

HRID 1602086 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>O1CCCC1>[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 are dissolved in 420 ml of absolute tetrahydrofuran. 233.5 ml (1.84 mol) of trimethylchlorosilane are added dropwise, while stirring, and 69.5 g (0.46 mol) of (R)-phenylglycine are then added in portions within the space of 4 hours. The reaction mixture is stirred at room temperature overnight. 690 ml of methanol are then added and the mixture is stirred at room temperature for 2 hours and concentrated in vacuo. The residue is dissolved, while stirring, in 690 ml of a 20% aqueous solution of potassium hydroxide. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulphate and concentrated in vacuo.

Workup

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

Sources & evidence

ORD record
ord-62bef2d833174e03baf16a0eb74b762d
Source dataset
uspto-grants-1999_11
Patent number
US05981492

Reaction notes

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