Bioactivities (1007)
Yield
Reactions (14)
Substances (15)
Conditions
Targets (53)
Citations (15)
References
1
Synthesize Find similar With potassium borohydride in methanol; water
T=-10 - -5°C; Inert atmosphere; Hide Experimental Procedure
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Rx-ID: 45012213
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Zhejiang Apeloa Kangyu Pharmaceutical Co., Ltd.; Wang, Zheqing; Ge, Mengya; Ye, Zengfaang; Shu, Lijian; Zheng, Liangrong; Fang, Meifen; Sun, Yunlei; Zhang, Kehua
Patent: CN106008183 A, 2016 ; Location in patent: Paragraph 01021; 0122; 0123 ; Title/Abstract Full Text Show Details
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 °).
2
Synthesize Find similar Multi-step reaction with 2 steps 1: potassium borohydride / water; methanol / -10 - -5 °C / |Inert atmosphere 2: hydrogenchloride / water / pH 1 View Scheme
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Rx-ID: 45012214
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Zhejiang Apeloa Kangyu Pharmaceutical Co., Ltd.; Wang, Zheqing; Ge, Mengya; Ye, Zengfaang; Shu, Lijian; Zheng, Liangrong; Fang, Meifen; Sun, Yunlei; Zhang, Kehua
Patent: CN106008183 A, 2016 ; Title/Abstract Full Text Show Details
3
Synthesize Find similar Multi-step reaction with 3 steps 1: |Inert atmosphere 2: potassium borohydride / water; methanol / -10 - -5 °C / |Inert atmosphere 3: hydrogenchloride / water / pH 1 View Scheme
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Rx-ID: 45012227
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Zhejiang Apeloa Kangyu Pharmaceutical Co., Ltd.; Wang, Zheqing; Ge, Mengya; Ye, Zengfaang; Shu, Lijian; Zheng, Liangrong; Fang, Meifen; Sun, Yunlei; Zhang, Kehua
Patent: CN106008183 A, 2016 ; Title/Abstract Full Text Show Details
4
Synthesize Find similar With sodium tetrahydroborate
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Rx-ID: 36491911
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Salouros, Helen; Sutton, Gordon J.; Howes, Joanna; Hibbert, D. Brynn; Collins, Michael
Analytical Chemistry, 2013 , vol. 85, # 19 p. 9400 - 9408 Title/Abstract Full Text View citing articles Show Details
5
Synthesize Find similar Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: |Acidic conditions View Scheme
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Rx-ID: 36491912
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Salouros, Helen; Sutton, Gordon J.; Howes, Joanna; Hibbert, D. Brynn; Collins, Michael
Analytical Chemistry, 2013 , vol. 85, # 19 p. 9400 - 9408 Title/Abstract Full Text View citing articles Show Details
A
B
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6
Synthesize Find similar Rx-ID: 393870
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B: 0.098 g
With sodium amalgam
Fourneau; Kanao
Bulletin de la Societe Chimique de France, 1924 , vol. <4> 35, p. 620 Full Text View citing articles Show Details
Eberhard
Archiv der Pharmazie (Weinheim, Germany), 1915 , vol. 253, p. 89 Full Text Show Details
Kanao
Chem. Zentralbl., 1927 , vol. 98, # I p. 2538 Full Text Show Details
With zinc(II) tetrahydroborate in diethyl ether
T=-78°C; 1 h;
Fraser, David S.; Park, Sheldon B.; Chong, J. Michael
Canadian Journal of Chemistry, 2004 , vol. 82, # 2 p. 87 - 101 Title/Abstract Full Text View citing articles Show Details
7
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Rx-ID: 10040209
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Kurashima, Naoki; Makino, Yukiko; Sekita, Setsuko; Urano, Yasuteru; Nagano, Tetsuo
Analytical Chemistry, 2004 , vol. 76, # 14 p. 4233 - 4236 Title/Abstract Full Text View citing articles Show Details
8
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Rx-ID: 393871
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With palladium
Hydrogenation;
Merck,E.
Patent: DE472466 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2835 Full Text Show Details
With aluminum isopropoxide; isopropyl alcohol
Hendriks, Iris E.; Wilson; Meekan
Coral Reefs, 2001 , vol. 20, # 1 p. 77 - 84 Title/Abstract Full Text View citing articles Show Details
9
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10
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Rx-ID: 437423
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With lithium aluminium tetrahydride
Takamatsu
Yakugaku Zasshi, 1956 , vol. 76, p. 1227 Chem.Abstr., 1957 , p. 4304 Full Text View citing articles Show Details
With sodium tetrahydroborate
Takamatsu
Yakugaku Zasshi, 1956 , vol. 76, p. 1227 Chem.Abstr., 1957 , p. 4304 Full Text View citing articles Show Details
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Multi-step reaction with 2 steps 2: NaBH4
View Scheme
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Rx-ID: 22224125
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Takamatsu
Yakugaku Zasshi, 1956 , vol. 76, p. 1227 Chem.Abstr., 1957 , p. 4304 Full Text View citing articles Show Details
11
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Rx-ID: 7912723
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P=1520 - 2280 Torr; Hydrogenation;
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Hyde; Browning; Adams
Journal of the American Chemical Society, 1928 , vol. 50, p. 2290 Full Text View citing articles Show Details
A
B
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12
Synthesize Find similar Rx-ID: 7912724
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T=0 - 5°C;
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Fourneau; Kanao
Bulletin de la Societe Chimique de France, 1924 , vol. <4> 35, p. 620 Full Text View citing articles Show Details
Kanao
Yakugaku Zasshi, 1927 , # 540 p. 18 Chem. Zentralbl., 1927 , vol. 98, # I p. 2539 Full Text View citing articles Show Details
Eberhard
Archiv der Pharmazie (Weinheim, Germany), 1915 , vol. 253, p. 89 Full Text Show Details
13
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Rx-ID: 7912720
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unter geringem Ueberdruck.Hydrogenation;
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Eberhard
Archiv der Pharmazie (Weinheim, Germany), 1920 , vol. 258, p. 104 Full Text Show Details
Merck
Patent: DE472466 ; Full Text Show Details
14
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Rx-ID: 7912719
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Hydrogenation;
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Merck
Patent: DE469782 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2908 Full Text Show Details