Phenyl Glycinol (Made according to Literature Prep for (S)-tert-Leucinol (Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A., J. Org. Chem., 1998, 63, 4541-4544.)),
Iodomethane (Aldrich),
THF (distilled from potassium),
NaH (Aldrich, washed with dry ether then dry pentane).

D-(-)-a-Phenylglycinol (2.00 g, 14.6 mmol) was dissolved in dry THF (20 ml) and was added dropwise to a stirred suspension of sodium hydride (0.72 g, 30.0 mmol, 2.05 eq) in dry THF (10 ml). The solution was stirred for 1 h at ambient temperature. Iodomethane (0.96 ml, 15.4 mmol) was added dropwise and the solution was stirred for 1 h at ambient temperature. At this point, the solution was heated to reflux (65oC) for a further 2 h before cooling to ambient temperature, followed by the addition of brine (40 ml). The product was extracted with diethyl ether (4 × 60 ml), dried over sodium sulphate and the solvent was removed to leave a clear oil (crude yield = 1.80 g). This crude product was purified by Kugelrohr distillation to give a clear oil (bp 70oC under high vacuum). Purified yield = 1.38 g, 9.1 mmol, 63%.

1H NMR (300 MHz, 298 K, CDCl3) 7.33-7.16 (5H, m, Ph), 4.12 (1H, dd, 3JHH = 4 Hz, 9 Hz, CH), 3.43 (1H, 2JHH = 5 Hz , 3JHH = 4 Hz, CH2), 3.32-3.26 (4H, m, CH2, CH3), 1.67 (2H, s, NH2). 13C{1H} NMR (75 MHz, 298 K, CDCl3) 142.56, 128.44, 127.40, 126.79, 79.01, 58.93, 55.42.

Bream, R. N.; Ley, S. V.; McDermott, B.; Procopiou, P. A. Journal of the Chemical Society-Perkin Transactions 1 2002, 2237-2242.

Evans, D. A.; Peterson, G. S.; Johnson, J. S.; Barnes, D. M.; Campos, K. R.; Woerpel, K. A., J. Org. Chem., 1998, 63, 4541-4544.