(S)-1-(2-氨基-5-氯苯基)-1-三氟甲基-3-环丙基-2-丙炔-1-醇合成路线 （共 28 条）
反应条件
1: With (1R,2S)-N-pyrrolidinyl norephedrine; dimethyl zinc in toluene 1 h; 2: With methanol in toluene 0.5 h; 3: cyclopropyl acetylene; 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone With n-butyl-magnesium chloride Product distribution / selectivity; more than 3 stages;
参考文献
MERCK and CO., INC.
Patent: EP981520 B1, 2004 ;
Location in patent: Page 23; 25; 26 ;
反应条件
1: With methanol; (1R,2S)-N-pyrrolidinyl norephedrine; dimethyl zinc in toluene T=20°C; 9 h; 2: With citric acid in water; toluene Product distribution / selectivity;
参考文献
MERCK and CO., INC.
Patent: EP1017666 B1, 2003 ;
Location in patent: Page/Page column 6; 11-12 ;
反应条件
1: With methanol; (+-)-erythro-2-dibenzylamino-1-phenyl-propanol-(1); dimethyl zinc in toluene 9 h; 2: With citric acid in water; toluene Product distribution / selectivity;
参考文献
MERCK and CO., INC.
Patent: EP1017666 B1, 2003 ;
Location in patent: Page/Page column 6; 9-10 ;
反应条件
(1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide 1.) THF, toluene, hexane, 2.) THF, toluene, hexane; Yield givenMultistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
参考文献
Journal of Organic Chemistry, , vol. 63, # 23 p. 8536 - 8543
反应条件
1: With (1R,2S)-N-pyrrolidinyl norephedrine; dimethyl zinc in toluene T=-20 - 0°C; 0.5 h; 2: With 2,2-dimethyl-propanol in toluene T=20 - 60°C; 1.5 h; 3: 1-chloro-4-pentyne; 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone With n-butyl-magnesium chloride Product distribution / selectivity; more than 3 stages;
参考文献
MERCK and CO., INC.
Patent: EP981520 B1, 2004 ;
Location in patent: Page 29 ;
反应条件
1: With methanol; (1R,2S)-N-pyrrolidinyl norephedrine; dimethyl zinc in toluene T=20°C; 9 h; 2: With citric acid in water; toluene Product distribution / selectivity;
参考文献
MERCK and CO., INC.
Patent: EP1017666 B1, 2003 ;
Location in patent: Page/Page column 6; 12 ;
反应条件
1: With methanol; (1R,2S)-N-pyrrolidinyl norephedrine; dimethyl zinc in toluene T=20°C; 9 h; 2: With citric acid in water; toluene Product distribution / selectivity;
参考文献
MERCK and CO., INC.
Patent: EP1017666 B1, 2003 ;
Location in patent: Page/Page column 6; 12 ;
反应条件
hydrogenchloride; sodium hydroxide in methanol; water
参考文献
DuPont Pharmaceuticals Company
Patent: US5932726 A1, 1999 ;
反应条件
iron; acetic acid in tetrahydrofuran; methanol T=20°C; 5 h; Inert atmosphere; chemoselective reaction;
参考文献
Kawai, Hiroyuki; Kitayama, Takashi; Tokunaga, Etsuko; Shibata, Norio
European Journal of Organic Chemistry, 2011 , # 30 p. 5959 - 5961
反应条件
1: With methanol; (+/-)-2-dimethylamino-1-phenyl-1-propanol; dimethyl zinc in toluene 9 h; 2: With citric acid in water; toluene Product distribution / selectivity;
参考文献
MERCK and CO., INC.
Patent: EP1017666 B1, 2003 ;
Location in patent: Page/Page column 6; 9-10 ;
