Stereoselective synthesis of (±)-threo-2-amino-1-(4-nitrophenyl)-1, 3-propanediol

O Červinka, V Dudek, A Fábryová, J Kolář…

Index: Cervinka, Otakar; Dudek, Vaclav; Fabryova, Anna; Kolar, Jiri; Lukac, Juraj; et al. Collection of Czechoslovak Chemical Communications, 1989 ,  vol. 54,  # 10  p. 2748 - 2752

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Citation Number: 4

Abstract

Abstract Addition of hypobromic acid to styrene afforded styrene bromohydrin (I) which was dehydrated to ω-bromostyrene (II). Prince reaction of II with aqueous formaldehyde gave 5- bromo-4-phenyl-1, 3-dioxane (III). The bromine atom in III was replaced with amino group by treatment with methanolic ammonia at 150 C and 6–8 MPa and the obtained threo-5-amino- 4-phenyl-1, 3-dioxane (IVa) was hydrolyzed to give (±)-threo-2-amino-1-phenyl-1, 3- ...