Query Query
1. Query H
OH
H
NH
Results
Date
20 reactions in Reaxys
2016-09-09 05h:01m:17s (EST)
20 reactions in Reaxys
2016-09-09 05h:02m:06s (EST)
Search as: As drawn, No mixtures, No charges, No radicals 2. Query
(1. Query) AND itemno in (1)
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OH H
O
H 2N
H
OH
H
NH
H
N H
Rx-ID: 806751 View in Reaxys 1/20 Yield
Conditions & References With benzene Foltz; Witkop; Journal of the American Chemical Society; vol. 79; (1957); p. 201,203 View in Reaxys Belzecki; Lange; Roczniki Chemii; vol. 28; (1954); p. 561,563, 567, 568; ; (1955); p. 6871 View in Reaxys Belzecki; Lange; Roczniki Chemii; vol. 33; (1959); p. 703,704, 709; ; (1960); p. 2236 View in Reaxys Fourneau; Benoit; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 985,988 View in Reaxys
HN O O
H
OH
H
NH
Rx-ID: 32043573 View in Reaxys 2/20 Yield
Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, T= -5 °C , Reflux Nag, Sangram; Lehmann, Lutz; Heinrich, Tobias; Thiele, Andrea; Kettschau, Georg; Nakao, Ryuji; Gulyas, Balazs; Halldin, Christer; Journal of Medicinal Chemistry; vol. 54; nb. 20; (2011); p. 7023 - 7029 View in Reaxys
H N
H
OH
H
H
OH
H
NH
Rx-ID: 394193 View in Reaxys 3/20 Yield
Conditions & References With hydrogenchloride, T= 100 °C Spaeth; Goehring; Monatshefte fuer Chemie; vol. 41; (1920); p. 325 View in Reaxys
O HO
OH H
N H HO
H H
OH H HO
O
H
OH
H
NH
Rx-ID: 3210532 View in Reaxys 4/20 Yield
Conditions & References in dimethyl sulfoxide, T= 25 °C , Equilibrium constant Zingg, S. P.; Arnett, Edward M.; McPhail, Andrew T.; Bothner-By, Aksel A.; Gilkerson, W. R.; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1565 - 1580
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View in Reaxys
O
HO
OH
H N
H
OH OH
HO O
H
OH
H
NH
Rx-ID: 3210536 View in Reaxys 5/20 Yield
Conditions & References in dimethyl sulfoxide, T= 25 °C , Equilibrium constant Zingg, S. P.; Arnett, Edward M.; McPhail, Andrew T.; Bothner-By, Aksel A.; Gilkerson, W. R.; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1565 - 1580 View in Reaxys
(1S:2R)-2-<methyl-benzyl-amino>-1-phenyl-propanol-(1)-hydrochloride
H
OH
H
NH
Rx-ID: 7584305 View in Reaxys 6/20 Yield
Conditions & References With ethanol, palladium, Hydrogenation Patent; I.G. Farbenind.; DE538455; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 3046 View in Reaxys With water, palladium, Hydrogenation Patent; I.G. Farbenind.; DE538455; (1930); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 18; p. 3046 View in Reaxys
(R)-2-methylamino-1-phenyl-propanone-(1) H
OH
H
NH
Rx-ID: 7584306 View in Reaxys 7/20 Yield
Conditions & References With water, palladium, Hydrogenation Patent; I.G. Farbenind.; DE639126; (1935); Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 23; p. 481 View in Reaxys
H
OH
H
NH
H
OH
H
NH
racemate
Rx-ID: 438165 View in Reaxys 8/20 Yield
Conditions & References With Petroleum ether, β-D-lactose, benzene, durch Chromathographie
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Lecoq; Bulletin de la Societe Royale des Sciences de Liege; vol. 12; (1943); p. 316 View in Reaxys
H
OH
H
NH
salt of (-)-ephedrine H
OH
H
NH
racemate
Rx-ID: 7925132 View in Reaxys 9/20 Yield
Conditions & References With dextrorotatory α-lt;4-arsono-anilinogt;-propionic acid amide, ergibt das Salz des (+)-Ephedrins Fourneau; Nicolitch; Bulletin de la Societe Chimique de France; vol. <4> 43; (1928); p. 1239 View in Reaxys
O
H N
H
OH
H
NH
Rx-ID: 36491911 View in Reaxys 10/20 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
O
H
OH
H
NH
Rx-ID: 36491916 View in Reaxys 11/20 Yield
Conditions & References Reaction Steps: 2 1: bromine 2: sodium tetrahydroborate With sodium tetrahydroborate, bromine 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
OH
H
NH
H N
H
OH
H
H
OH
H
NH
racemate
Rx-ID: 2198865 View in Reaxys 12/20 Yield
Conditions & References Brown; Moudachirou; Tetrahedron; vol. 50; nb. 34; (1994); p. 10309 - 10320
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View in Reaxys Schmid; Wirnsberger; Guebitz; Pharmazie; vol. 51; nb. 11; (1996); p. 852 - 854 View in Reaxys
H N
OH erythro erythro
Cl
H
H
OH
H
NH
Rx-ID: 3605591 View in Reaxys 13/20 Yield
Conditions & References Prelog, Vladimir; Mutak, Stjepan; Helvetica Chimica Acta; vol. 66; nb. 7; (1983); p. 2274 - 2278 View in Reaxys Prelog, Vladimir; Mutak, Stjepan; Kovacevic, Krunoslav; Helvetica Chimica Acta; vol. 66; nb. 7; (1983); p. 2279 2284 View in Reaxys
O
H 2N
(1R,2S)-1-methylamino-1-phenyl-propan-2-ol H
OH
H
NH
Rx-ID: 5508938 View in Reaxys 14/20 Yield
Conditions & References Foltz; Witkop; Journal of the American Chemical Society; vol. 79; (1957); p. 201,203 View in Reaxys Belzecki; Lange; Roczniki Chemii; vol. 28; (1954); p. 561,563, 567, 568; ; (1955); p. 6871 View in Reaxys Belzecki; Lange; Roczniki Chemii; vol. 33; (1959); p. 703,704, 709; ; (1960); p. 2236 View in Reaxys Fourneau; Benoit; Bulletin de la Societe Chimique de France; vol. <5> 12; (1945); p. 985,988 View in Reaxys
heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with (+)-ephedrine
H 2N
H
OH
H
NH
heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with n-propylamine
Rx-ID: 8741186 View in Reaxys 15/20 Yield
Conditions & References in methanol, water, Kinetics Grigorean; Lebrilla; Analytical Chemistry; vol. 73; nb. 8; (2001); p. 1684 - 1691 View in Reaxys
H H 2N
OH
heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with (+)-ephedrine
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H
OH
H
NH
heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with (R)-1-amino-2-propanol
Rx-ID: 8747021 View in Reaxys 16/20 Yield
Conditions & References in methanol, water, Kinetics Grigorean; Lebrilla; Analytical Chemistry; vol. 73; nb. 8; (2001); p. 1684 - 1691 View in Reaxys
H H 2N
permethylated maltoheptaose, complex with (+)-ephedrine
OH
H
OH
H
NH
permethylated maltoheptaose, complex with (R)-1-amino-2-propanol
Rx-ID: 8747022 View in Reaxys 17/20 Yield
Conditions & References in methanol, water, Kinetics Grigorean; Lebrilla; Analytical Chemistry; vol. 73; nb. 8; (2001); p. 1684 - 1691 View in Reaxys
H 2N HO
H
O
H
OH
H
NH
Rx-ID: 36491918 View in Reaxys 18/20 Yield
Conditions & References Acidic conditions 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
OH
H
NH
Rx-ID: 7584304 View in Reaxys 19/20 Yield
Conditions & References Stork et al.; Tetrahedron Letters; (1979); p. 771,773 View in Reaxys Each of the following compounds exhibited a significant dose- and time-effect, with an interaction of dose and time (all Fs>2.7; all p values <0.01): (+)-amphetamine, (-)-ephedrine,
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(+)-ephedrine, (-)-norpseudoephedrine, (+)-norpseudoephedrine and mephentermine. Patent; Booth, Anthony; Caffrey, James L.; US2003/105332; (2003); (A1) English View in Reaxys 2 : Fluorodehydroxylation of D-Ephedrine EXAMPLE 2 Fluorodehydroxylation of D-Ephedrine D-Ephedrine, subjected to the same conditions as in Example 1, resulted a mixture of erythro-fluorodehydroxy-Dephedrine and threo-fluorodeoxy-D-ephedrine, in the form of hydrochloride salt. Patent; Merck and Co., Inc.; US4096180; (1978); (A1) English View in Reaxys
O
H
OH
H
NH
O
Rx-ID: 24904552 View in Reaxys 20/20 Yield
Conditions & References 3 : 3R-Formyltetrahydropyran EXAMPLE 3 3R-Formyltetrahydropyran Title product of Example 1 (48.1 g) and H2 O (1 liter) were stirred at 23° C. Dissolution was almost complete after 10 minutes and was complete after less than 1 hour. The initially observed pH was 3.21. It rose to 3.48 after 10 minutes, to 4.09 after 1 hour and 4.32 after 2 hours, where it remained constant over the ensuing 0.5 hour. After stirring for a total of 2.5 hours, the aqueous solution was extracted 1*364 ml CH2 Cl2 and 3*150 ml CH2 Cl2. The four organic layers were combined, dried (MgSO4) and stripped to yield present title product as a colorless oil, 8.8 g; [alpha]D 23 =+2.84° (c=0.634, CHCl3). (+)-Ephedrine is recovered from the mother liquor by basification and extraction into CH2 Cl2. Title product is prepared in like manner from the corresponding p-toluenesulfonate salt. 3S-Formyltetrahydropyran, having equal but opposite sign of rotation, is prepared in like manner from the R-camphorsulfonic acid salt or the p-toluenesulfonate salt of 3,4S-dimethyl-5R-phenyl-2S-(3S-tetrahydropyranyl)-oxazolidine. Patent; Pfizer Inc; US5149821; (1992); (A1) English View in Reaxys
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