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Reduction of phenylglycine; amino alcohol

SyntheticPage 275
DOI: 10.1039/SP275
Submitted Jun 03, 2008, published Jun 03, 2008
Suzanne Elizabeth Howson (

			Reaction Scheme: Reduction of phenylglycine

Chemicals Used

NaBH4 (Fisher Scientific),
Iodine (Sigma Aldrich),
Phenylglycine (Sigma Aldrich),
KOH (Fisher Scientific),
THF (distilled over potassium).


Sodium borohydride (31.21 g, 0.825 mol) in a dry three-necked round-bottom flask was put under Argon and dry THF (400 ml) was added. The solution was stirred whilst phenylglycine (50.00 g, 0.33 mol) was added as a solid in one portion. The flask was cooled to 0oC using an ice-water bath and fitted with a reflux condenser. Iodine (83.75 g, 0.33 mol) in dry THF (100 ml) was added dropwise to the solution. The reaction was then stirred at ambient temperature for 2 h, before heating to reflux (80oC) overnight. Methanol (~400 ml) was added slowly until the solution became clear. All solvent was then removed on the rotary evaporator to leave a white paste, which was then dissolved in aqueous 20% potassium hydroxide solution (600 ml) and stirred at ambient temperature overnight. The product was extracted into dichloromethane (5 x 250 ml), dried over sodium sulphate and the solvent removed to leave the crude product (crude yield = 48.00 g). The product was recrystallised from hot toluene. Yield = 23.33 g, 0.17 mol, 52%.

Author's Comments

Adapted from prep for (S)-tert-Leucinol.


1H NMR (400 MHz, 298 K, CDCl3) 7.30-7.18 (5H, m, Ph), 3.97 (1H, dd, 3JHH = 4 Hz, 8 Hz), 3.66 (1H, dd, 2JHH = 11 Hz, 3JHH = 4 Hz, CH2), 3.48 (1H, dd, 2JHH = 11 Hz , 3JHH = 8 Hz, CH2), 2.05 (2H, s, NH2).

Lead Reference

Evans, Peterson, Johnson, Barnes, Campos and Woerpel, J. Org. Chem., 1998, 63, 4541.

Supplementary Information

1H NMR (seh.jcamp)

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Keywords: alcohol, amino acid, Phenylglyicol, Reduction, Sodium Borohydride

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