通过催化加氢连续流合成 syn-2-Amino-1,3-二醇：(+)-甲砜霉素和 (+)-氟苯尼考的重要中间体,Organic Process Research & Development

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通过催化加氢连续流合成 syn-2-Amino-1,3-二醇：(+)-甲砜霉素和 (+)-氟苯尼考的重要中间体
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2022-08-17 , DOI: 10.1021/acs.oprd.2c00100
Yingqi Xia ₁ , Baijun Ye ₂ , Minjie Liu ₂ , Meifen Jiang ₂ , Fener Chen _{1,

2}

Affiliation

本文报道了一种快速有效的连续流动工艺合成顺-2-氨基-1,3-二醇。起始原料syn -2-nitro-1,3-diol 在装有阮内镍催化剂的微型固定床反应器中与氢气反应，以 93% 的分离产率提供syn -2-amino-1,3-diol。由于增强的传质，流动系统中的反应时间显着减少（从分批 36 小时到流动 5 分钟）。催化剂、溶剂、反应温度、反应时间、压力和 H _2的影响流量已被陆续研究。以阮内镍为催化剂，反应温度为 25 ℃，反应压力为 10 bar，反应溶剂为 3% AcOH 的甲醇溶液，H ₂流量时，连续流动反应的最佳条件如下：流速为 25 sccm，液体流速为 0.6 mL/min。研究了10-40°C温度范围内的反应动力学。测定反应速率常数和活化能。连续流动系统允许在百克规模上对顺-2-硝基-1,3-二醇进行有效加氢，在连续运行超过 240 小时后，总产率为 73.6 g/d。

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Continuous-Flow Synthesis of syn-2-Amino-1,3-diol via Catalytic Hydrogenation: A Vital Intermediate of (+)-Thiamphenicol and (+)-Florfenicol

In this paper, an expeditious and efficient continuous-flow process is reported for the synthesis of syn-2-amino-1,3-diol. The starting material syn-2-nitro-1,3-diol reacts with hydrogen gas in a micro fixed-bed reactor packed with a Raney Ni catalyst to provide syn-2-amino-1,3-diol in 93% isolated yield. The reaction time in the flow system was markedly reduced (from 36 h in batch to 5 min in flow) due to enhanced mass transfer. The effects of the catalyst, solvent, reaction temperature, reaction time, pressure, and H₂ flow rate have been investigated successively. The optimum conditions for the continuous-flow reaction are described as follows when using Raney Ni as a catalyst at a reaction temperature of 25 °C, a reaction pressure of 10 bar, a reaction solvent of 3% AcOH in methanol, an H₂ flow rate of 25 sccm, and a liquid flow rate of 0.6 mL/min. The reaction kinetics in the temperature range of 10–40 °C were investigated. The reaction rate constants and activation energy were determined. The continuous flow system allows for an efficient hydrogenation of syn-2-nitro-1,3-diol on the hectogram scale, corresponding to an overall productivity of 73.6 g/d after continuous operation for over 240 h.

更新日期：2022-08-17

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