Tetrahydrofuran → (S)-1-Phenyl-3-propanolamine

HRID 1059829

Reaction equation

HRID 1059829 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[NH2:8][C@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][C:11](OCC)=[O:12].C1COCC1>O>[NH2:8][C@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 22831526(S)-Ethyl 3-amino-3-phenylpropanoate hydrochloride

Product 1

HCID 2734520(S)-1-Phenyl-3-propanolamineYield 80.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.45 g (38.1 mmol) of lithium aluminum hydride were added in portions with ice-cooling to a suspension of 3.5 g (15.2 mmol) of ethyl (S)-3-amino-3-phenyl-propionate hydrochloride in 150 ml or absolute THF and the mixture was stirred at room temperature for 1 hour. 5 ml of water were then cautiously added dropwise with ice-cooling. The precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was taken up in DCM and the solution was extracted with water. The organic phase was dried over sodium sulfate. After filtration and removal of the solvent in vacuo, 1.84 g of (S)-3-amino-3-phenylpropanol were obtained.

Workup

  1. temperaturecooling
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. extractionthe solution was extracted with water
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationAfter filtration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-79e7c204029c4b759876bab0adcabff0
Source dataset
uspto-grants-2003_02
Patent number
US06521654B2

Linked notes

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