CN101973891B - 一种手性(R)-α-苯乙胺盐酸盐的制备及合成方法 - Google Patents

一种手性(R)-α-苯乙胺盐酸盐的制备及合成方法 Download PDF

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CN101973891B
CN101973891B CN 201010534445 CN201010534445A CN101973891B CN 101973891 B CN101973891 B CN 101973891B CN 201010534445 CN201010534445 CN 201010534445 CN 201010534445 A CN201010534445 A CN 201010534445A CN 101973891 B CN101973891 B CN 101973891B
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罗梅
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Liuan Jianuo Biochemical Technology Co., Ltd
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Abstract

一种新型手性(S)-α-苯乙胺盐酸盐化合物，该化合物的合成方法是(S)-α-苯乙胺与六水合氯化钴在无水乙醇溶液中反应一天，将反应液热过滤，自然挥发滤液，得到产物手性(S)-α苯乙胺盐酸盐。该化合物在苯甲醛的腈硅化反应中显示良好的催化性能，其产率高达90％。

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一种手性(R)-α-苯乙胺盐酸盐的制备及合成方法
一、技术领域
本发明涉及一种季铵盐的制备及合成方法，确切地说是一种手性α-苯乙胺盐酸盐的制备及合成方法。 
二、背景技术
季铵盐的合成方法已有许多文献报道。早在1956年，J.Chem.Soc.报道了一些季铵盐的合成方法，1959年，J.Am.Chem.Soc.也报道了季铵盐类的合成方法。(1.Surrey，Alexander R.；Lesher，George Y.；Mayer，J.Richard；Webb，Wm.G.Journal of the American Chemical Society(1959)，812894-7；2.Davis，M.Journal of the Chemical Society(1956)，337-43.)。 
申请人在合成手性(S)-α-苯乙胺与六水合氯化钴配合物的实验中，未得到目标产物配合物，却得到了另一种新型手性化合物(R)-α-苯乙胺盐酸盐。 
三、发明内容
本发明旨在提供手性化合物(R)-α-苯乙胺盐酸盐，所要解决的技术问题是一步合成得到目标产物。 
本发明所称的一种手性(R)-α-苯乙胺盐酸盐是由(S)-α-苯乙胺与六水合氯化钴制备的由以下化学式所示的化合物： 
Figure GSB0000112593140000011
化学名称：(R)-α-苯乙胺盐酸盐，简称化合物(I)。 
本合成方法包括合成和分离，所述的合成2.32：1的(S)-α-苯乙胺与六水合氯化钴在无水乙醇溶液中反应48小时，将反应液热过滤，自然挥发滤液，得到产物手性(R)-α-苯乙胺盐酸盐无色晶体。 
本合成方法一步得到目标产物，工艺简单，操作方便。 
四、附图说明
图1是(R)-α-苯乙胺盐酸盐的X-衍射分析图。 
五、具体实施方式
1.手性(R)-α-苯乙胺盐酸盐的制备 
在100mL烧瓶中，无水无氧条件下，加入六水合氯化钴2.3793g(10mmol)，(S)-α-苯乙胺3mL(23.2mmol)，无水乙醇30mL，将混合物回流24h，停止反应，反应液热过滤，自然挥发滤液，得到产物手性(R)-α-苯乙胺盐酸盐无色晶体。熔点：78-79℃，[a]5 D＝-12.71°(c1.18，C2H5OH)，1HNMR(300MHz，CDCl3)：8.60(s，3H)，7.26-7.47(m，5H)，4.34(s，1H)，1.64(s，3H).13CNMR(75MHz，CDCl3)137.76，129.13，128.95，52.02，20.96.，IR：3428，2982，2918，2738，2681，2634，2579，2492，2037，1600，1511，1498，1455，1385，1291，1229，1091，1066，1031，769，749，699，529.元素分析结果如下：理论值：C，60.95％；H，7.676％；N，8.886％，实测值：C，60.45％；H，7.484％；N，8.789％. 
2.腈硅化反应应用 
2-苯基-2-(三甲硅氧基)丙腈的制备 
0.20mmol化合物I，苯甲醛0.1mL，TMSCN0.3ml(3.3mmol)相继在20～30℃下加入，120h后，经柱层析后(石油醚/二氯甲烷：5/1)，得无色油状液体，产率：90％，1HNMR(300MHz，CDCl3)7.56-7.59(m，0.9Hz，2H)，7.31-7..34(m，3H)，5.43(s，1H)，0.16(s，9H).13CNMR(75MHz，CDCl3)136.1，128.8(x2)，126.2(x2)，119.1，63.5，-0.39(x3). 
Figure GSB0000112593140000021

Claims (1)

1.一种手性(R)-α-苯乙胺盐酸盐的合成方法，包括合成和分离，其特征在于在100mL烧瓶中，无水无氧条件下，加入六水合氯化钴2.3793g(10mmol)，(S)-α-苯乙胺3mL(23.2mmol)，无水乙醇30mL，将混合物回流24h，停止反应，反应液热过滤，自然挥发滤液，得到产物手性(R)-α-苯乙胺盐酸盐无色晶体。
CN 201010534445 2010-11-04 2010-11-04 一种手性(R)-α-苯乙胺盐酸盐的制备及合成方法 Expired - Fee Related CN101973891B (zh)

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CN102329240A (zh) * 2011-07-01 2012-01-25 罗梅 一种间苯二甲胺二盐酸盐的制备及合成方法
CN102503835A (zh) * 2011-11-14 2012-06-20 罗梅 一种铵盐的合成方法
CN104788330B (zh) * 2015-03-25 2017-03-22 合肥工业大学 一种手性双l‑亮氨酸盐酸盐的制备及合成方法
CN105130827A (zh) * 2015-09-24 2015-12-09 合肥祥晨化工有限公司 一种手性（r）-苯甘氨醇盐酸盐的合成方法

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Iridium/Monodentate Phosphoramidite Catalyzed Asymmetric Hydrogenation of N-Aryl Imines;Natasa Mrsic et al.;《J. AM. CHEM. SOC.》;20090601;第131卷(第24期);第8358–8359页 *
John T. Colyer et al..Reversal of Diastereofacial Selectivity in Hydride Reductions of N-tert-Butanesulfinyl Imines.《J. Org. Chem》.2006,第71卷(第18期),第6859-6862页.
Natasa Mrsic et al..Iridium/Monodentate Phosphoramidite Catalyzed Asymmetric Hydrogenation of N-Aryl Imines.《J. AM. CHEM. SOC.》.2009,第131卷(第24期),第8358–8359页.
Reversal of Diastereofacial Selectivity in Hydride Reductions of N-tert-Butanesulfinyl Imines;John T. Colyer et al.;《J. Org. Chem》;20060811;第71卷(第18期);第6859-6862页 *
蔡其勇.基础化学实验.《基础化学实验》.西南交通大学出版社,2006,第137页. *

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