Scalable, Green Synthesis of Heteroaromatic Amine-boranes,Organic Process Research & Development

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Scalable, Green Synthesis of Heteroaromatic Amine-boranes
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-03-28 , DOI: 10.1021/acs.oprd.3c00031
P. Veeraraghavan Ramachandran ₁ , Henry J. Hamann ₁ , Randy Lin ₁ , Aman Singh ₁

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In situ generated, transient sodium monohydroxyborohydride readily reacts with a present amine to form amine-borane adducts in ethyl acetate at room temperature. Synthesis of heteroaromatic pyridine-, 2-picoline-, and 5-ethyl-2-methylpyridine-boranes, those relevant to large-scale reductive aminations, has been demonstrated at 100 mmol scale, and pyridine-borane at 1.1 mole scale. This first report substituting ethyl acetate for tetrahydrofuran, the traditional solvent for amine-borane synthesis, allows for activation of sodium borohydride by the aqueous portion of the heterogeneous dual-solvent system. These factors make this green protocol more economical than those currently available for the large-scale production of amine-boranes as demonstrated, quantitatively, by the computed green chemistry metrics.

中文翻译：

杂芳胺-硼烷的可扩展绿色合成

在室温下，原位生成的瞬态单羟基硼氢化钠很容易与存在的胺反应，在乙酸乙酯中形成胺-硼烷加合物。与大规模还原胺化相关的杂芳基吡啶-、2-甲基吡啶-和 5-乙基-2-甲基吡啶-硼烷的合成已在 100 毫摩尔规模和吡啶-硼烷在 1.1 摩尔规模下得到证明。第一份报告用乙酸乙酯代替胺-硼烷合成的传统溶剂四氢呋喃，允许通过非均相双溶剂系统的水部分激活硼氢化钠。这些因素使这种绿色协议比目前可用于大规模生产胺硼烷的协议更经济，正如计算的绿色化学指标在数量上所证明的那样。

更新日期：2023-03-28

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