Enantioselective Synthesis of (R)-Salbutamol Hydrochloride

Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (12): 1558-1561. Previous Articles Next Articles

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盐酸(R)-沙丁胺醇的不对称合成

程青芳*^,a,b，王启发^c，许兴友^a,b，叶燕斌^a，张辉^a

(^a淮海工学院化工系连云港 222005)
(^b南京理工大学材料化学实验室南京 210094)
(^c淮海工学院海洋学院连云港 222005)

收稿日期:2007-03-06 修回日期:2007-05-08 发布日期:2007-12-04
通讯作者: 程青芳

Enantioselective Synthesis of (R)-Salbutamol Hydrochloride

CHENG Qing-Fang*^,a,b, WANG Qi-Fa^c, XU Xing-You^a,b, YE Yan-Bin^a
ZHANG Hui^a

(^a Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005)
(^b Materials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094)
(^c College of Marine Science, Huaihai Institute of Technology, Lianyungang 222005)

Received:2007-03-06 Revised:2007-05-08 Published:2007-12-04
Contact: CHENG Qing-Fang

Abstract

The enantioselective synthesis of (R)-salbutamol hydrochloride was investigated. The asymmetric epoxidation of 3-acetoxymethyl-4-acetyloxystyrene (1) catalyzed by chiral camphyl β-diketone iron complex enantioselectively afforded (R)-3-acetoxymethyl-4-acetyloxy styrene oxide (2) in good yield and enantioselectivity. In following steps, styrene oxide 2 was converted into (R)-salbutamol hydrochloride in 68% overall yield via the ring-opening of chiral terminal styrene oxide 2 with t-butylamine and then with hydrochloride. Some factors effecting the yield and the enantioselectivity of asymmetric epoxidation of 3-acetoxymethyl-4- acetyloxystyrene (1) were discussed.

Key words: camphyl β-diketone, iron complex, asymmetric epoxidation, (R)-salbutamol hydrochloride

Cite this article

CHENG Qing-Fang*^,a,b, WANG Qi-Fa^c, XU Xing-You,b, YE Yan-Bin^a
ZHANG Hui^a. Enantioselective Synthesis of (R)-Salbutamol Hydrochloride[J]. Chin. J. Org. Chem., 2007, 27(12): 1558-1561.

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盐酸(R)-沙丁胺醇的不对称合成

Enantioselective Synthesis of (R)-Salbutamol Hydrochloride

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