Query Query Cl
Date
14 reactions in Reaxys
2016-09-09 04h:51m:56s (EST)
14 reactions in Reaxys
2016-09-09 04h:52m:34s (EST)
H OH
H
1. Query
Results
H N H
Search as: As drawn, No mixtures, No charges, No radicals 2. Query
(1. Query) AND itemno in (1)
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2016-09-09 04:57:54
H N
OH
H
H N
H
OH Cl
H
H
H
Rx-ID: 41227785 View in Reaxys 1/14 Yield
Conditions & References
52 mg
(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol hydrochloride (1): To a solution of benzyl carbamate 16 (0.10 g) in methanol was added 10percent Pd/C (10 mg). The resulting solution was stirred under hydrogen (1 atmosphere) for 12 h at room temperature until completion of the reaction as monitored by thin-layer chromatography (TLC). The reaction mixture was filtered through a celite pad to remove the catalyst, and the filtrate was concentrated in vacuo to get (1R, 2S)-ephedrine as colourless oil to which methanolic HCl (3N, 3mL) was added and stirred for 30 min. The reaction mixture was concentrated to give (1R, 2S)-ephedrine hydrochloride 1 as a colorless solid (52 mg). With hydrochlorid acid in methanol, Time= 0.5h, p= 760.051Torr , enantioselective reaction Lalwani, Komal G.; Sudalai, Arumugam; Tetrahedron Letters; vol. 56; nb. 46; (2015); p. 6488 - 6490 View in Reaxys
HO
N
O
H
H
H N
H
H N
OH Cl
H
H
HO
O N
HO
OH OH
O O
Rx-ID: 3239207 View in Reaxys 2/14 Yield
Conditions & References
52 %, 64 %
With hydrogen, palladium on activated charcoal in ethanol, Time= 25h, p= 1500.1Torr , Ambient temperature Hussain; Wyatt; Tetrahedron; vol. 49; nb. 10; (1993); p. 2123 - 2130 View in Reaxys
H N
O
2H
O H
OH O
Cl
ephedrine salt
H N
H
OH Cl
H
H
Cl
Rx-ID: 24361498 View in Reaxys 3/14 Yield 40%
Conditions & References 5 : EXAMPLE 5 EXAMPLE 5 8.25 g (50 mmol) of D,L-ephedrine and 5.88 g (25 mmol) of D-2,4-dichlorophenoxypropionic acid were taken up in 100 ml of toluene. Heating to reflux was followed by slow cooling, and the crystals were filtered off with suction and washed with toluene. Drying resulted in 4.2 g (42percent) of ephedrine salt. Liberation of the base as in Example 1 and conversion thereof into the hydrochloride resulted in L-ephedrine hydrochloride in an overall yield of 40percent, [α]D 20: -33.7°. Patent; BASF Aktiengesellschaft; US6015903; (2000); (A1) English View in Reaxys
Copyright © 2016 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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H N
OH
H
(1S,2R)-1-methylamino-1-phenyl-propan-2-ol (C10H15NO)
H
H N
H
OH Cl
H
H
Rx-ID: 19593545 View in Reaxys 4/14 Yield
Conditions & References Reaction Steps: 4 1: 4 Angstroem molecular sieves / CH2Cl2 / 24 h / Ambient temperature 2: 1) 4 Angstroem molecular sieves, 2) tetrabutylammonium periodate / 1) dichloromethane, room temperature, 24 h, 2) dichloromethane, -65 deg C to room temperature, 2 h 3: 49 percent / barium chlorate monohydrate / osmium(VIII) oxide / H2O; 2-methyl-propan-2-ol / 28 h / 20 °C 4: 52 percent / H2 / 5percent palladium on carbon / ethanol / 25 h / 1500.1 Torr / Ambient temperature With barium chlorate monohydrate, 4 A molecular sieve, hydrogen, tetrabutylammonium (meta)periodate, palladium on activated charcoal, osmium(VIII) oxide in ethanol, dichloromethane, water, tert-butyl alcohol Hussain; Wyatt; Tetrahedron; vol. 49; nb. 10; (1993); p. 2123 - 2130 View in Reaxys
N
H N
O
H
OH Cl
H
H
E E
Rx-ID: 19623484 View in Reaxys 5/14 Yield
Conditions & References Reaction Steps: 3 1: 1) 4 Angstroem molecular sieves, 2) tetrabutylammonium periodate / 1) dichloromethane, room temperature, 24 h, 2) dichloromethane, -65 deg C to room temperature, 2 h 2: 49 percent / barium chlorate monohydrate / osmium(VIII) oxide / H2O; 2-methyl-propan-2-ol / 28 h / 20 °C 3: 52 percent / H2 / 5percent palladium on carbon / ethanol / 25 h / 1500.1 Torr / Ambient temperature With barium chlorate monohydrate, 4 A molecular sieve, hydrogen, tetrabutylammonium (meta)periodate, palladium on activated charcoal, osmium(VIII) oxide in ethanol, water, tert-butyl alcohol Hussain; Wyatt; Tetrahedron; vol. 49; nb. 10; (1993); p. 2123 - 2130 View in Reaxys
O
O N
H N
H
OH Cl
H
H
O H O
H N
Rx-ID: 19625713 View in Reaxys 6/14 Yield
Conditions & References Reaction Steps: 2 1: 49 percent / barium chlorate monohydrate / osmium(VIII) oxide / H2O; 2-methyl-propan-2-ol / 28 h / 20 °C 2: 52 percent / H2 / 5percent palladium on carbon / ethanol / 25 h / 1500.1 Torr / Ambient temperature With barium chlorate monohydrate, hydrogen, palladium on activated charcoal, osmium(VIII) oxide in ethanol, water, tert-butyl alcohol Hussain; Wyatt; Tetrahedron; vol. 49; nb. 10; (1993); p. 2123 - 2130
Copyright © 2016 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.
3/6
2016-09-09 04:57:54
View in Reaxys
H N
N-methyl-<l-ephedrine>
OH
H
Cl
H
H
Rx-ID: 8241951 View in Reaxys 7/14 Yield
Conditions & References With hydrogenchloride Schmidt; Archiv der Pharmazie (Weinheim, Germany); vol. 252; (1914); p. 57 View in Reaxys Schmidt; Eberhard; Archiv der Pharmazie (Weinheim, Germany); vol. 253; (1915); p. 64,66 View in Reaxys
H
N H H
Cl
Cl
H N
H
OH
H
Cl
H
H
N
Rx-ID: 29573659 View in Reaxys 8/14 Yield
Conditions & References With water, sodium hydroxide, Time= 24h Cruz, Alejandro; Padilla-Martinez, Itzia Irene; Garcia-Baez, Efren V.; Tetrahedron Asymmetry; vol. 21; nb. 8; (2010); p. 909 - 913 View in Reaxys
H
N H H
Cl
Cl
H N
H
Cl H HN
OH
H
H
OH Cl H
H
N
H
Rx-ID: 29573658 View in Reaxys 9/14 Yield
Conditions & References With ammonia, water, Time= 8h, Reflux Cruz, Alejandro; Padilla-Martinez, Itzia Irene; Garcia-Baez, Efren V.; Tetrahedron Asymmetry; vol. 21; nb. 8; (2010); p. 909 - 913 View in Reaxys hydrochloric acid H N
H
d-pseudoephedrine-O-sulfuric acid ester
OH Cl H
H
d-pseudoephedrine hydrochloride
Rx-ID: 8275716 View in Reaxys 10/14 Yield
Conditions & References Schmidt; Archiv der Pharmazie (Weinheim, Germany); vol. 252; (1914); p. 121; Archiv der Pharmazie (Weinheim, Germany); vol. 253; (1915); p. 52 View in Reaxys
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Cl
Cl
Cl
Cl
H N
OH
H
H N
OH
H
Cl
H
H
H
Rx-ID: 61101 View in Reaxys 11/14 Yield
Conditions & References Steldt; Chen; Journal of the American Pharmaceutical Association (1912-1977); vol. 29; (1940); p. 106 View in Reaxys
Cl
Cl
H N
OH
H
Cl
H N
OH
H
Cl
H
H
H
Rx-ID: 211597 View in Reaxys 12/14 Yield
Conditions & References Krishna; Ghose; Journal of the Society of Chemical Industry, London; vol. 48; (1929); p. 67,69 View in Reaxys
Cl Cl
Cl
H N
Cl
H
OH H N
OH Cl
H
H
H
Cl
H
Rx-ID: 220790 View in Reaxys 13/14 Yield
Conditions & References Miller; Journal of the American Pharmaceutical Association (1912-1977); vol. 37; (1948); p. 226 View in Reaxys
H N
H
OH Cl
H
H
Rx-ID: 25212568 View in Reaxys 14/14 Yield
Conditions & References 1.C : STEP C: STEP C: Hemisuccinate of d-allethrolone A solution of 35 ml of an aqueous hydrochloric acid solution of 22° Be in 250 ml of water was added with stirring to a suspension of 150 g of the dextro ephedrine salt of the hemisuccinate of d-allethrolone in 750 ml of benzene at 20° C and after stirring for 1 hour, 2 phases formed. The aqueous phase containing ephedrine hydrochloride was separated by decantation and was reextracted with benzene. The combined benzene extracts were dried and distilled to dryness under reduced pressure. Patent; Roussel-UCLAF; US4005146; (1977); (A1) English View in Reaxys The resolution of the enantiomers of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid was carried out via reaction with the following chiral bases: Brucine Quinine (-)-Cinchonidine (+)-Cinchonine R-(+)-1-Phenylethylamine (1 R,2S)-(-)-Ephedrine hydrochloride (1S,2R)-(+)-Ephedrine hydrochloride. Patent; Laboratorios del Dr. Esteve S.A.; EP1944294; (2008); (A1) English
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2016-09-09 04:57:54
View in Reaxys
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