引用本文:
张宝华, 史兰香. (R)-1-(4-苄氧基-3-硝基苯基)-2-溴乙醇制备工艺的改进[J]. 应用化学,
2013, 30(11): 1369-1371.
doi:
10.3724/SP.J.1095.2013.30005
Citation: ZHANG Baohua, SHI Lanxiang. New Preparation Process for (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-Bromoethanol[J]. Chinese Journal of Applied Chemistry, 2013, 30(11): 1369-1371. doi: 10.3724/SP.J.1095.2013.30005
Citation: ZHANG Baohua, SHI Lanxiang. New Preparation Process for (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-Bromoethanol[J]. Chinese Journal of Applied Chemistry, 2013, 30(11): 1369-1371. doi: 10.3724/SP.J.1095.2013.30005
(R)-1-(4-苄氧基-3-硝基苯基)-2-溴乙醇制备工艺的改进
摘要:
以4-苄氧基-3-硝基-α-溴代苯乙酮为原料,在聚苯乙烯磺酰胺化固载的(R)-二苯基脯氨醇形成的唑硼烷催化下,经NaBH4/Me3SiCl不对称还原制得了(R,R)-福莫特罗的关键中间体(R)-1-(4-苄氧基-3-硝基苯基)-2-溴乙醇,收率95%,ee值95.4%。手性氨基醇可以方便的分离和回收利用,降低了生产成本。用NaBH4/Me3SiCl为还原剂代替BH3,降低了毒性,提高了安全性。
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关键词:
- (R)-(苄氧基-硝基苯基)-溴乙醇
- / NaBH4/Me3SiCl
- / 不对称还原
- / 固载(R)-二苯基脯氨醇
English
New Preparation Process for (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-Bromoethanol
Abstract:
(R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol,a key intermediate for the preparation of (R,R)-formoterol,was prepared from 4-benzyloxy-3-nitrophenyl-α-bromoacetophenone using BH3 complex with polymer-bonded (R)-diphenylpyrrolidinemethanol as the catalyst and NaBH4/Me3SiCl as reductant via an enantioselective reduction. The yield and ee value for the reaction are 95% and 95.4% respectively. The resulted chiral compounds can be easily separated and recycled,which reduce the production cost. Using NaBH4/Me3SiCl as the reductant could minimize the toxicity of the reaction and help to improve the safety issue.
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