(RR)及(SS)-2-氨基-1,2-二苯基乙醇的合成

Synthesis of(RR)and(SS)-2-amino-1,2-diphenyl Ethanol

光学纯的2-氨基-1,2-二苯基乙醇是一类用途广泛的手性β-氨基醇,在手性药物的研发与手性配体的合成等领域有着重要的用途。分别以(RS及SR)-2-氨基-1,2-二苯基乙醇作为原料,通过6步反应,获得了手性的(RR)及(SS)-2-氨基-1,2-二苯基乙醇。反应途径主要包括Boc基团保护氨基、PCC试剂氧化羟基、Ni+H_(2)还原法还原酮羰基、乙酰基保护羟基、碱性条件脱Ac保护基团和酸性条件下脱除Boc基团。产物结构经过^(1)H NMR和^(13)C NMR分析表征。

Optically pure 2-amino-1,2-diphenyl ethanol is a kind of chiral β -amino alcohols, which is widely used in the field of chiral drugs development and the synthesis of chiral ligands. In this paper, chiral( RR ) and( SS )- 2-amino-1,2-diphenyl ethanol was obtained with( RS and SR )-2-amino-1,2-diphenyl ethanol as raw material by a 6-step reaction. The reaction pathway mainly includes Boc group protecting amino group, PCC reagent oxidizing hydroxyl group, Ni+H_(2) reducing ketocarbonyl group, acetyl group protecting hydroxyl group, alkaline condition removing Ac protection group and acidic condition removing Boc group. These compounds were characterized by ^(1)H NMR and ^(13)C NMR.