(2S)-2-Amino-1-(3-fluorophenyl)-4-methyl-pentane-1-ol hydrochloride → (2S)-2-Amino-1-(3-fluorophenyl)-4-methyl-pentane-1-ol

HRID 13128Notes

Reaction equation

HRID 13128 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1)[OH:5]>[OH-].[Na+].C(OCC)(=O)C>[NH2:2][C@@H:3]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1)[OH:5]

Participants

4

Reactant 1

HCID 66812770(2S)-2-Amino-1-(3-fluorophenyl)-4-methyl-pentane-1-ol hydrochloride

Product 1

HCID 66812540(2S)-2-Amino-1-(3-fluorophenyl)-4-methyl-pentane-1-ol

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

(2S)-2-Amino-1-(3-fluorophenyl)-4-methyl-pentane-1-ol hydrochloride (1.6 g, 6.46 mmol) is stirred overnight in a mixture of 1N NaOH (12.92 mL) and ethyl acetate (20 mL). The organic phase is separated and the aqueous phase is washed twice with ethyl acetate. The combined organic extracts are washed with brine, dried over Na2SO4 and the solvent is evaporated. After purification of the residue by chromatography (silicagel, eluents: dichloromethane/methanol) 694 mg (50.9%) of the title compound as mixture of stereoisomers is obtained.

Workup

  1. customThe organic phase is separated
  2. washthe aqueous phase is washed twice with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated
  6. customAfter purification of the residue by chromatography (silicagel, eluents: dichloromethane/methanol) 694 mg (50.9%) of the title compound
  7. additionas mixture of stereoisomers
  8. customis obtained

Sources & evidence

ORD record
ord-cf178acfffb24dbe8683f5766c107c05
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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