Sodium Hydroxide → (S)-2-Amino-4-phenoxy-butan-1-ol

HRID 885151Notes

Reaction equation

HRID 885151 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@@H:10]([NH2:20])[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>O1CCCC1>[NH2:20][C@@H:10]([CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][OH:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67177678methyl (2S)-2-amino-4-phenoxybutanoate

Product 1

HCID 20677773(S)-2-Amino-4-phenoxy-butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of lithium aluminum hydride (282 mg) in tetrahydrofuran (4 ml) was added a solution of (S)-2-amino-4-phenoxy-butyric acid methyl ester (778 mg) in tetrahydrofuran (3 ml) and the mixture was stirred for 2 hours at 50° C. Sodium hydroxide solution (4N) was added until gas evolution ceased and the suspension was filtered through Celite. The solvent was evaporated and the residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=98:2) to yield a colourless oil, (180 mg, 27%); MS (ISP): 182.3 ((M+H)+).

Workup

  1. filtrationthe suspension was filtered through Celite
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=98:2)
  4. customto yield a colourless oil, (180 mg, 27%)

Sources & evidence

ORD record
ord-318bbfc8a23d40c398fd62cd8fba8b65
Source dataset
uspto-grants-2012_08
Patent number
US08242153B2

Reaction notes

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