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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence