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0 °C

L-Alanine methyl ester hydrochloride (9.9 g, 70.9 mmol) was added portionwise to a 1.0 M solution of phenylmagnesium bromide (78.0 g, 0.43 mol) in THF at 0° C. and then heated under reflux for 21 h. The reaction mixture was cooled to 0° C., quenched with dropwise addition of saturated NH4Cl, and stirred for 1 h. After collecting insoluble products through the Buchner funnel, organic products were extracted into AcOEt (3×100 ml). The combined organic extracts were dried over K2CO3/MgSO4, and concentrated under reduced pressure to obtain a crude product. Impurities were washed with dichloromethane over silica gel by means of dry-flash column chromatography, further elution with a mixture of AcOEt and petrol, ranging from 20% up to 100%, gave the title compound (10) (1.16 g, 9%) as a white solid. m.p. 100–101° C. (litii,v 100–102° C.). [α]D25=−85.59° (c, 0.0362 in CHCl3) (litii: −82.38° (c, 0.814 in CHCl3; litv: −85.9° (c, 2.77 in CHCl3). δH 0.94 (3H, d, 3J=6.30 Hz, CH3), 1.23 (2H, broad s, NH2), 4.15 (1H, q, 3J=6.30 Hz, CH—NH2), 4.25 (1H, broad s, OH), 7.10–7.66 (10H, m, Ar—H). δC 17.4 (CH3), 52.1 (CH—NH2), 78.7 (C—OH), 125.7, 126.1, 126.6, 126.9, 128.2 and 128.7 (o-, m- and p-Ar), 145.0 and 147.2 (α-Ar). Anal. Calcld. for C15H17NO: C 79.26; H 7.54; N 6.16. Found: C 79.30; H 7.66; N 6.27. ir 3432 (OH), 3389 (NH2). m/e (CI—NH3) 228 (MH+, 100%).

1. temperatureheated
2. temperatureunder reflux for 21 h
3. customquenched with dropwise addition of saturated NH4Cl
4. customAfter collecting insoluble products through the Buchner funnel, organic products
5. extractionwere extracted into AcOEt (3×100 ml)
6. dry with materialThe combined organic extracts were dried over K2CO3/MgSO4
7. concentrationconcentrated under reduced pressure
8. customto obtain a crude product
9. washImpurities were washed with dichloromethane over silica gel by means of dry-flash column chromatography, further elution with a mixture of AcOEt and petrol