Query Query O
1. Query
HN
Results
Date
14 reactions in Reaxys
2017-11-28 21h:33m:58s (EST)
HO
HN
Search as: As drawn, No salts, No mixtures
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O
HO
O 2
O HN
O
HO
OH
O 2
O
O HN
O
O
O
OH
O
O
O OH
Rx-ID: 45012213 View in Reaxys 1/14 Yield
Conditions & References 10 : Example 10 (S) - (-) - 2-methylamino-1-phenyl-acetone-DBTA complex salt (233.2 g, 0.34 mol) was placed in a reaction flask under nitrogen.A 50percent by volume aqueous solution of methanol (700 ml) was added and stirred at room temperature to form a clear solution.Cooled to -10 to -5 ° C and then adding potassium borohydride powder and maintaining the same low temperature reaction for 30 to 60 minutes.HPLC showed the disappearance of the starting material, the reaction was concentrated under reduced pressure and evaporated to dryness. Ice water (500 ml) was added to the residue, and then 5N concentrated hydrochloric acid was added dropwise to pH = 1.0.The precipitated (-) - DBTA was extracted twice with ethyl acetate.A 10 N aqueous solution of sodium hydroxide was added dropwise to an acidic aqueous solution which had been cooled to 0 to 5 ° C until pH = 12.The precipitated oil was extracted three times with toluene.The combined organic phases were washed once with water and once with saturated brine.5N hydrochloric acid was added dropwise to a toluene solution to pH = 5-6 and stirred for 15 minutes.The layers were separated and concentrated under reduced pressure to dryness to give ephedrine (1) hydrochloride (124.6 g, 91.1percent, specific rotation -34.5 °). With potassium borohydride in methanol, water, T= -10 - -5 °C , Inert atmosphere Patent; Zhejiang Apeloa Kangyu Pharmaceutical Co., Ltd.; Wang, Zheqing; Ge, Mengya; Ye, Zengfaang; Shu, Lijian; Zheng, Liangrong; Fang, Meifen; Sun, Yunlei; Zhang, Kehua; (13 pag.); CN106008183; (2016); (A) Chinese View in Reaxys
O
HO
O 2
2
O HN
O
O
OH
O
HCl
O
HN
OH
Rx-ID: 45012214 View in Reaxys 2/14 Yield
Conditions & References Reaction Steps: 2 1: potassium borohydride / water; methanol / -10 - -5 °C / |Inert atmosphere 2: hydrogenchloride / water / pH 1 With hydrogenchloride, potassium borohydride in methanol, water Patent; Zhejiang Apeloa Kangyu Pharmaceutical Co., Ltd.; Wang, Zheqing; Ge, Mengya; Ye, Zengfaang; Shu, Lijian; Zheng, Liangrong; Fang, Meifen; Sun, Yunlei; Zhang, Kehua; (13 pag.); CN106008183; (2016); (A) Chinese View in Reaxys
H N
O
OH
Cl
H
2
HCl HN
Rx-ID: 45012227 View in Reaxys 3/14 Yield
Conditions & References Reaction Steps: 3 1: |Inert atmosphere 2: potassium borohydride / water; methanol / -10 - -5 °C / |Inert atmosphere 3: hydrogenchloride / water / pH 1 With hydrogenchloride, potassium borohydride in methanol, water
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Patent; Zhejiang Apeloa Kangyu Pharmaceutical Co., Ltd.; Wang, Zheqing; Ge, Mengya; Ye, Zengfaang; Shu, Lijian; Zheng, Liangrong; Fang, Meifen; Sun, Yunlei; Zhang, Kehua; (13 pag.); CN106008183; (2016); (A) Chinese View in Reaxys
H N
O
H
OH
H
NH
Rx-ID: 36491911 View in Reaxys 4/14 Yield
Conditions & References With sodium tetrahydroborate Salouros, Helen; Sutton, Gordon J.; Howes, Joanna; Hibbert, D. Brynn; Collins, Michael; Analytical Chemistry; vol. 85; nb. 19; (2013); p. 9400 - 9408 View in Reaxys
H N
O
H N
OH
H
H
Rx-ID: 36491912 View in Reaxys 5/14 Yield
Conditions & References Reaction Steps: 2 1: sodium tetrahydroborate 2: |Acidic conditions With sodium tetrahydroborate Salouros, Helen; Sutton, Gordon J.; Howes, Joanna; Hibbert, D. Brynn; Collins, Michael; Analytical Chemistry; vol. 85; nb. 19; (2013); p. 9400 - 9408 View in Reaxys
H N
O
H HN
OH
H
OH
H
H
NH
racemate
racemate
Rx-ID: 393870 View in Reaxys 6/14 Yield
Conditions & References With sodium amalgam Fourneau; Kanao; Bulletin de la Societe Chimique de France; vol. <4> 35; (1924); p. 620 View in Reaxys Eberhard; Archiv der Pharmazie (Weinheim, Germany); vol. 253; (1915); p. 89 View in Reaxys Kanao; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 2538 View in Reaxys
0.098 g
With zinc(II) tetrahydroborate in diethyl ether, Time= 1h, T= -78 °C Fraser, David S.; Park, Sheldon B.; Chong, J. Michael; Canadian Journal of Chemistry; vol. 82; nb. 2; (2004); p. 87 - 101 View in Reaxys
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O
H N
OH
H N
Rx-ID: 10040209 View in Reaxys 7/14 Yield
Conditions & References With hydrogen Kurashima, Naoki; Makino, Yukiko; Sekita, Setsuko; Urano, Yasuteru; Nagano, Tetsuo; Analytical Chemistry; vol. 76; nb. 14; (2004); p. 4233 - 4236 View in Reaxys
O
H N
H
OH
H
NH racemate
Rx-ID: 393871 View in Reaxys 8/14 Yield
Conditions & References With palladium, Hydrogenation Patent; Merck,E.; DE472466; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 2835 View in Reaxys With aluminum isopropoxide, isopropyl alcohol Hendriks, Iris E.; Wilson; Meekan; Coral Reefs; vol. 20; nb. 1; (2001); p. 77 - 84 View in Reaxys
H N
O
H N
H
OH
H
H
Rx-ID: 437423 View in Reaxys 9/14 Yield
Conditions & References With lithium aluminium tetrahydride Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1227; ; (1957); p. 4304 View in Reaxys With sodium tetrahydroborate Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1227; ; (1957); p. 4304 View in Reaxys
H N
O
H N
H
OH
H
Rx-ID: 22224125 View in Reaxys 10/14 Yield
Conditions & References Reaction Steps: 2 2: NaBH4 With sodium tetrahydroborate Takamatsu; Yakugaku Zasshi; vol. 76; (1956); p. 1227; ; (1957); p. 4304 View in Reaxys
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H N
OH
O
platinum oxide
H
OH
H
NH racemate
Rx-ID: 7912723 View in Reaxys 11/14 Yield
Conditions & References p= 1520 - 2280Torr , Hydrogenation Hyde; Browning; Adams; Journal of the American Chemical Society; vol. 50; (1928); p. 2290 View in Reaxys
H N
Cl
O
sodium amalgam
H
H HN
OH
H
OH
H
H
NH racemate
racemate
Rx-ID: 7912724 View in Reaxys 12/14 Yield
Conditions & References T= 0 - 5 °C Fourneau; Kanao; Bulletin de la Societe Chimique de France; vol. <4> 35; (1924); p. 620 View in Reaxys Kanao; Yakugaku Zasshi; nb. 540; (1927); p. 18; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 2539 View in Reaxys Eberhard; Archiv der Pharmazie (Weinheim, Germany); vol. 253; (1915); p. 89 View in Reaxys
O
H N
H
O
H
palladium/charcoal
H
OH
H
NH racemate
Rx-ID: 7912720 View in Reaxys 13/14 Yield
Conditions & References unter geringem Ueberdruck.Hydrogenation Eberhard; Archiv der Pharmazie (Weinheim, Germany); vol. 258; (1920); p. 104 View in Reaxys Patent; Merck; DE472466 View in Reaxys
OH
H N
O
nickel
H
OH
H
NH racemate
Rx-ID: 7912719 View in Reaxys 14/14 Yield
Conditions & References Hydrogenation Patent; Merck; DE469782; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 16; p. 2908
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View in Reaxys
Copyright © 2017 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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