Sodium Nitrite → (r)-3-(4-fluorophenyl)-beta-alaninol

HRID 1416883Notes

Reaction equation

HRID 1416883 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:12][CH2:13][OH:14])C(O)=O)=[CH:4][CH:3]=1.[N:15]([O-])=O.[Na+]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:15])[CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 54078727HCID 54078727, compound

Product 1

HCID 10197883(r)-3-(4-fluorophenyl)-beta-alaninol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

The hydrazide of (R)-2-(4fluorophenyl)-4-hydroxybutanoic acid (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5° C., followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (R)-1-(4-fluorophenyl)-3-hydroxypropylamine is isolated as a light yellow oil.

Workup

  1. extractionextraction of the reaction mixture with ethyl acetate
  2. extractionfollowed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether
  3. dry with materialdrying of the extracts over MgSO4, filtration
  4. customthe removal of solvent
  5. customby rotary evaporation

Sources & evidence

ORD record
ord-9cdaa105425747e7bbe695df514f3008
Source dataset
uspto-grants-1999_06
Patent number
US05916786

Reaction notes

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