Sodium Nitrite → (3S)-3-Amino-3-(4-fluorophenyl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

The hydrazide of (S)-2-(4-fluorophenyl)-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 (S)-1-(4fluorophenyl)-3-hydroxypropylamine is isolated as a light yellow oil.

Provenance & Evidence