Query Query
Results
Date
17 reactions in Reaxys
2017-10-17 20h:23m:28s (EST)
17 reactions in Reaxys
2017-10-17 20h:25m:58s (EST)
O H N
1. Query
OH
O
Search as: As drawn 2. Query
(1. Query) AND NOT itemno in (12,11,6,5)
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.
1/7
2017-10-17 20:46:43
Cl
O
O
H N
HN O
O O
O OH
O
O
Rx-ID: 326982 View in Reaxys 1/17 Yield
Conditions & References With ammonium hydroxide, Erhitzen des Reaktionsprodukts mit wss. HCl McCord et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 5693,5696 View in Reaxys
O H N
N
N
O OH
O
O
Rx-ID: 2821311 View in Reaxys 2/17 Yield
Conditions & References
55 %
acid hydrolysis Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland; Tetrahedron Letters; vol. 22; (1981); p. 141 - 144 View in Reaxys Stage 1: With sodium hydroxide, Time= 3h, T= 20 °C Stage 2: With hydrogenchloride, Time= 100h, T= 16 °C Zink, Charles N.; Kim, Hyun-Joong; Fishbein, James C.; Journal of Organic Chemistry; vol. 71; nb. 1; (2006); p. 202 - 209 View in Reaxys
O Cl
O
H N
O OH
OH NH 2
O
Rx-ID: 3727693 View in Reaxys 3/17 Yield
Conditions & References With triethylamine in methanol, Time= 7h, T= 64 °C Kogami; Okawa; Bulletin of the Chemical Society of Japan; vol. 60; nb. 8; (1987); p. 2963 - 2965 View in Reaxys
O Cl
O
H N
O
OH NH 2
OH
O
Rx-ID: 3727694 View in Reaxys 4/17 Yield 97.3 %
Conditions & References With triethylamine in methanol, Time= 7h, T= 64 °C Kogami; Okawa; Bulletin of the Chemical Society of Japan; vol. 60; nb. 8; (1987); p. 2963 - 2965 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.
2/7
2017-10-17 20:46:43
H
NH 2
HO
O
H N
O
OH
NH 2
O
O
Rx-ID: 10212295 View in Reaxys 5/17 Yield
Conditions & References With Pseudomonas putida N-methyl-L-amino acid dehydrogenase, T. viride L-lysine oxidase, Tris buffer, Adenineflavine dinucleotide, catalase in various solvent(s), Time= 72h, T= 30 °C , pH= 8.2 Yasuda, Mari; Ueda, Makoto; Muramatsu, Hisashi; Mihara, Hisaaki; Esaki, Nobuyoshi; Tetrahedron Asymmetry; vol. 17; nb. 12; (2006); p. 1775 - 1779 View in Reaxys
H N
O O
O H N
O
O OH
O O
Cl
Rx-ID: 18335369 View in Reaxys 6/17 Yield
Conditions & References Reaction Steps: 2 1: 77 percent / H2 / Pd black / methanol / 0.5 h 2: 97.3 percent / Et3N / methanol / 7 h / 64 °C With hydrogen, triethylamine, palladium in methanol Kogami; Okawa; Bulletin of the Chemical Society of Japan; vol. 60; nb. 8; (1987); p. 2963 - 2965 View in Reaxys
H N
O O
O H N
O
O OH
O O
Cl
Rx-ID: 18335370 View in Reaxys 7/17 Yield
Conditions & References Reaction Steps: 2 1: H2 / Pd black / methanol / 0.5 h 2: Et3N / methanol / 7 h / 64 °C With hydrogen, triethylamine, palladium in methanol Kogami; Okawa; Bulletin of the Chemical Society of Japan; vol. 60; nb. 8; (1987); p. 2963 - 2965 View in Reaxys
OH O
O
O N
O
H N
O OH
O
Rx-ID: 37195339 View in Reaxys 8/17 Yield
Conditions & References With trifluoroacetic acid in dichloromethane, Time= 5h, T= 20 °C Blizzard, Timothy A.; Singh, Sanjay; Patil, Basanagoud; Chidurala, Naresh; Komanduri, Venukrishnan; Debnath, Samarpita; Belyakov, Sergei; Crespo, Alejandro; Struck, Alice; Kurtz, Marc; Wiltsie, Judyann; Shen,
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.
3/7
2017-10-17 20:46:43
Xun; Sonatore, Lisa; Arocho, Marta; Lewis, Dale; Ogletree, Martin; Biftu, Tesfaye; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 4; (2014); p. 1111 - 1115 View in Reaxys
O
H N
OH
O
Rx-ID: 37340387 View in Reaxys 9/17 Yield
Conditions & References
86 %
30 : [00236] Example 28:(38)_4_((6-(2-bromo_4-fhiorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydrOpYri midin-4-yI)methyl)morpholine-3-carboxylic acid General procedure: [00236] Example 28:(38)_4_((6-(2-bromo_4-fhiorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2yl)-3,6-dihydrOpYri midin-4-yI)methyl)morpholine-3-carboxylic acid A mixture of ethyl 4-(2-bromo-4-fluorophenyl)-6(bromomethyl)-2-(thiazol-2-yl)-1 ,4- dihydropyrimidine-5-carboxylate (7.7 g, 15.3 mmol), (S)-morpholine-3-carboxylic acid (2 g, 15.3 mmol) and potassium carbonate (4.23 g, 30.6 mmol) in anhydrous ethanol (154 mL)was stirred at 25 C for 16 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (V/V) 25/1) to give the title compound as a yellow solid (7.26 g, 86percent). The compound was characterized by the following spectroscopic data:MS-ESI: (ESI, pos.ion) m/z: 553.2 [M+ljH NMR (400 M1-lz, DMSO-d6): 12.90 (s, 111), 9.84 (s, 11-1), 8.04 (d, IH), 7.95 (d, IH),7.57-7.55 (m, 111), 7.43-7.37 (m, IH), 7.23-7J9 (m, 11-1), 6.03 (s, IH), 4.30-3.92 (m, 5H),3.84-3.82 (m, IH), 3.74-3.52 (m, 3H), 3.11-3.07 (m, IH), 2.55-2.39 (m, IH), 1.06 (t, 311). With potassium carbonate in ethanol, Time= 16h, T= 25 °C Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; LIU, Xinchang; SIEGFRIED, Goldmann; WO2014/29193; (2014); (A1) English View in Reaxys
H N
O
O OH
O
N H
O– Li+ O
Rx-ID: 29523869 View in Reaxys 10/17 Yield
Conditions & References Stage 1: With lithium hydroxide hydrate in methanol, water, Time= 2h, T= 20 °C Stage 2:Time= 2h, T= 20 °C Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis; Tetrahedron Asymmetry; vol. 21; nb. 5; (2010); p. 562 - 565 View in Reaxys
H N
O
O
O OH
N H
O– Na + O
Rx-ID: 29523870 View in Reaxys 11/17 Yield
Conditions & References Stage 1: With sodium hydroxide in methanol, water, Time= 2h, T= 20 °C Stage 2:Time= 2h, T= 20 °C Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis; Tetrahedron Asymmetry; vol. 21; nb. 5; (2010); p. 562 - 565 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.
4/7
2017-10-17 20:46:43
O Cl
O
H
N
O
H N
H
O
O H 2N
OH
H
Br
O
O Cl
OH
O
OH NH 2
NH 2
O
Rx-ID: 6925217 View in Reaxys 12/17 Yield
Conditions & References McCord et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 5693,5696 View in Reaxys
O
H
H
Cl
O
O
O
H
Br
N
H
H N
O
O OH
H
H 2N
O
O
OH
Cl
OH NH 2
NH 2
O
O
Rx-ID: 6925218 View in Reaxys 13/17 Yield
Conditions & References McCord et al.; Journal of the American Chemical Society; vol. 79; (1957); p. 5693,5696 View in Reaxys N
O
O
HN HCl
O
N
HO
O
O
Rx-ID: 44373753 View in Reaxys 14/17 Yield
Conditions & References
71 %
4.1.3. Morpholine-3-carboxylic acid hydrochloride (4) Compound 3 (76 g, 358 mmol) was added in several portions toa stirred concentrated hydrochloric acid (340 mmol), and theresulting mixture was refluxed for 10 h, cooled, and concentratedunder the reduced pressure. The residue was treated with KOH(76 g, 13.6 mol) in water (200 mL), stirred for 10 min, andconcentrated at 70 C. The residue was cooled and diluted with HCl(13.8 g, 13.6 mol), and the resulting mixture was concentratedunder reduced pressure. The crude solids, mixture of the productand ammonium chloride, were extracted with hot ethanol severaltimes. The combined fractions were concentrated under reducedpressure give the title compound 4 (42.8 g, 71percent) as white solid; m.p. 229e230; [Found: C, 35.75; H, 6.12; N, 8.15. C5H10ClNO3 requiresC, 35.83; H, 6.01; N, 8.36percent]; 1H NMR (DMSO-d6, 400 MHz):d 14.90e13.40 (br s, 1H), 10.57e9.00 (br s, 2H), 4.28e4.11 (m, 1H),4.06 (dd, J 12.2, 3.3 Hz, 1H), 3.97e3.55 (m, 3H), 3.21 (d, J 13.0 Hz,1H), 3.04 (t, J 9.0 Hz, 1H); 13C NMR (DMSO-d6, 125 MHz): d 167.6,64.8, 62.9, 54.0, 41.7. With hydrogenchloride, water, Time= 10h, Reflux Tereshchenko, Alexander D.; Myronchuk, Julia S.; Leitchenko, Lena D.; Knysh, Irina V.; Tokmakova, Ganna O.; Litsis, Olena O.; Tolmachev, Andrey; Liubchak, Konstantin; Mykhailiuk, Pavel; Tetrahedron; vol. 73; nb. 6; (2017); p. 750 - 757 View in Reaxys
H N
O
O
O OH
N H
O– K+ O
Rx-ID: 29523871 View in Reaxys 15/17 Yield
Conditions & References Stage 1: With potassium hydroxide in methanol, water, Time= 2h, T= 20 °C Stage 2:Time= 2h, T= 20 °C Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis; Tetrahedron Asymmetry; vol. 21; nb. 5; (2010); p. 562 - 565 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.
5/7
2017-10-17 20:46:43
O
O
H N
OH
O– Cs +
N H
O
O
Rx-ID: 29523872 View in Reaxys 16/17 Yield
Conditions & References Stage 1: With CsOH in methanol, water, Time= 2h, T= 20 °C Stage 2:Time= 2h, T= 20 °C Laars, Marju; Raska, Henri; Lopp, Margus; Kanger, Tonis; Tetrahedron Asymmetry; vol. 21; nb. 5; (2010); p. 562 - 565 View in Reaxys
O
O HO
O
HN
HCl HN
HCl HO
O
HO
S
O
O
O
N H
Rx-ID: 25341882 View in Reaxys 17/17 Yield
Conditions & References
10 g (22%) C.D : (D) (D) Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate A solution of 20 g (0.112 mole) of 4-methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22percent) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesised by the aforementioned procedure. Morpholine-3-carboxylic acid hydrochloride was prepared by the procedure described above, and has a melting point of 200°-2° C. With p-toluenesulfonic acid monohydrate, benzyl alcohol in benzene Patent; Mitsubishi Chemical Industries Limited; Okamoto; Shosuke; US4073913; (1978); (A1) English View in Reaxys Patent; Mitsubishi Chemical Industries Limited; Okamoto; Shosuke; US4097472; (1978); (A1) English View in Reaxys 10 g (22%) C.D : (D) (D) Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate A solution of 20 g (0.112 mole) of 4methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22percent) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesised by the aforementioned procedure. Morpholine-3-carboxylic acid hydrochloride was prepared by the procedure described above, and has a melting point of 200°-202° C. With p-toluenesulfonic acid monohydrate, benzyl alcohol in benzene Patent; Mitsubishi Chemical Industries Limited; Okamoto; Shosuke; US4101653; (1978); (A1) English View in Reaxys 10 g (22%) C.D : (D) (D) Benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate:
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.
6/7
2017-10-17 20:46:43
A solution of 20 g (0.112 mole) of 4-methyl-2-piperidinecarboxylic acid hydrochloride, 24 g (0.224 mole) of benzyl alcohol and 25.6 g (0.134 mole) of p-toluenesulfonic acid monohydrate in 100 ml of benzene was refluxed for 5 hours with the continuous removal of water through a Dean-Stark water trap. At the end of this period, the solvent was distilled off, and the residue was washed with ether-n-hexane and recrystallized to give 10 g (22percent) of benzyl 4-methyl-2-piperidinecarboxylate p-toluenesulfonate, M.P. 160°-163° C. The following 2-piperidinecarboxylates not previously reported in the chemical literature were synthesised by the aforementioned procedure. Morpholine-3-carboxylic acid hydrochloride was prepared by the procedure described above, and has a melting point of 200°-202° C. With p-toluenesulfonic acid monohydrate, benzyl alcohol in benzene Patent; Mitsubishi Chemical Industries Limited; Okamoto; Shosuke; US4093712; (1978); (A1) English 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.
7/7
2017-10-17 20:46:43