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[ CAS No. 28247-14-5 ]

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Chemical Structure| 28247-14-5
Chemical Structure| 28247-14-5
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CAS No. :28247-14-5 MDL No. :MFCD00019291
Formula : C9H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :167.21 g/mol Pubchem ID :-
Synonyms :

Safety of [ 28247-14-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 28247-14-5 ]

  • Downstream synthetic route of [ 28247-14-5 ]

[ 28247-14-5 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 28247-14-5 ]
  • [ 4254-02-8 ]
YieldReaction ConditionsOperation in experiment
at 510℃;
  • 2
  • [ 110-52-1 ]
  • [ 105-56-6 ]
  • [ 28247-14-5 ]
YieldReaction ConditionsOperation in experiment
98% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; water bath cooling; 68 Example 68; 5-Cvano-1-(3-trifluoromethoxybenzyl)-1H-indole-2-carboxylic acid (1- hydroxymethylcyclopentylmethyDamideEthyl cyanoacetate (2.5Og, 22mmol) and 1,4-dibromobutane (5.0Og, 23.0mmol) were dissolved in anhydrous DMF (20ml) under nitrogen and cesium carbonate (21.Og,64mmoles) added with water bath cooling. After stirring at room temperature for 18 h the reaction was diluted with water and extracted with ethyl acetate (2x80ml), the organic layers were combined and washed with water (40ml) and saturated aqueous sodium chloride solution (25ml). The organics were dried over magnesium sulphate, filtered and evaporated under reduced pressure to give 1-cyano-cyclopentanecarboxylic acid ethyl ester as an almost colourless oil (3.64g, 98%).
96% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;
82% With caesium carbonate In N,N-dimethyl-formamide at 0 - 25℃;
With sodium ethanolate
90 % Chromat. With tetrabutylammomium bromide In acetonitrile at 20℃; electrolytic synthesis in a diaphragm cell (Pt-cathode, carbon anode), I: ca. 80 mA, Q: ca. 2.2 F/mole;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 1h;
With potassium carbonate In acetonitrile for 96h; Heating;
13.75 gm (82%) With caesium carbonate In <i>N</i>-methyl-acetamide P.10 Ethyl 1-(cyano)cyclopentane-1-carboxylate Ethyl 1-(cyano)cyclopentane-1-carboxylate A suspension of 6.5 gm (200 mMol) cesium carbonate in 250 mL dimethylformamide containing 11.9 mL (100 mMol) 1,4-dibromobutane was cooled to 5° C. in an ice bath. A solution of 10.7 mL (100 mMol) ethyl cyanoacetate in 100 mL dimethylformamide was added dropwise over 25 minutes. The cooling bath was removed and the reaction mixture was stirred for 6 hours at room temperature. The reaction mixture was partitioned between hexane and water. The hexane phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was partitioned between methyl tert-butyl ether and water. The aqueous phase was washed with methyl tert-butyl ether and these organic phases are combined, washed with 3*100 mL 5% aqueous lithium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue was distilled under vacuum (11 mm Hg) through a Vigreaux column to provide 13.75 gm (82%) of the desired compound. b.p.=108-110° C. MS(FD): m/e=168 (M+1) EA: Calculated for: C9H13NO2: C, 64.65; H, 7.84; N, 8.38. Found: C, 64.53; H, 7.97; N, 8.56.
With sodium chloride; sodium ethanolate In diethyl ether; water 29.A A 24.88 g of ethyl cyanoacetate are added to the remaining half and the mixture is brought to the reflux point. 43.19 g of 1,4-dibromobutane are poured into another funnel and the solution of sodium ethylate and the 1,4-dibromobutane are simultaneously added dropwise to the reaction medium. When the addition is complete, reflux is maintained for 2 hours. The mixture is evaporated and the residue is taken up in an ethyl ether/water mixture, washed with a saturated solution of sodium chloride and then dried. The product obtained distils at 115°-120° C. under 11 mm of mercury.
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 2h;
With sodium ethanolate In ethanol at 70℃; for 4h;

Reference: [1]Current Patent Assignee: MERCK & CO INC - WO2006/100208, 2006, A1 Location in patent: Page/Page column 49
[2]Muthusamy, Sengodagounder; Gnanaprakasam, Boopathy [Tetrahedron Letters, 2005, vol. 46, # 4, p. 635 - 638]
[3]Varie, David L.; Shih, Chuan; Hay, David A; Andis, Sherri L.; Corbett, Tom H.; Gossett, Lynn S.; Janisse, Samantha K.; Martinelli, Michael J.; Moher, Eric D.; Schultz, Richard M.; Toth, John E. [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 3, p. 369 - 374]
[4]Morel; Stoll [Helvetica Chimica Acta, 1952, vol. 35, p. 2561,2565]
[5]Tatarinova, V. I.; Vasil'ev, A. A.; Petrosyan, V. A. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1990, vol. 39, # 11, p. 2399 - 2401][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 11, p. 2646 - 2648]
[6]Shia, Kak-Shan; Chang, Nien-Yin; Yip, Judy; Liu, Hsing-Jang [Tetrahedron Letters, 1997, vol. 38, # 44, p. 7713 - 7716]
[7]Fotouhi, Nader; Joshi, Pramod; Fry, David; Cook, Charles; Tilley, Jefferson W.; Kaplan, Gerry; Hanglow, Angela; Rowan, Karen; Schwinge, Virginia; Wolitzky, Barry [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1171 - 1173]
[8]Current Patent Assignee: WAYNE STATE UNIVERSITY; UNIVERSITY OF HAWAI&apos;I - US2002/128185, 2002, A1
[9]Current Patent Assignee: SANOFI - US5270317, 1993, A
[10]Ko, Yen-Chun; Zhu, Jia-Liang [Synthesis, 2007, # 23, p. 3659 - 3665]
[11]Location in patent: scheme or table Cowley, Phillip M.; Baker, James; Buchanan, Kirsteen I.; Carlyle, Ian; Clark, John K.; Clarkson, Thomas R.; Deehan, Maureen; Edwards, Darren; Kiyoi, Yasuko; Martin, Iain; Osbourn, Dawn; Walker, Glenn; Ward, Nick; Wishart, Grant [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2034 - 2039]
  • 3
  • [ 105-56-6 ]
  • [ 110-56-5 ]
  • [ 28247-14-5 ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate
  • 5
  • [ 28247-14-5 ]
  • [ 99065-34-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In ethanol
With hydrogen
With ammonia In aluminum nickel; ethanol 39.a N-(2-Ethoxycarbonyl-2,2-tetramethylen-ethyl)-N-pentanoyl-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-amine a) Ethyl 1-aminomethyl-cyclopentane-1-carboxylate is obtained by hydrogenating 33 g of ethyl 1-cyanocyclopentane-1-carboxylate (Alfred Bader Chemicals) in the presence of 10 g of Raney nickel, at 45° C. and under normal pressure in 330 ml of ethanol which contains about 4% ammonia. After filtering off the catalyst and removing the solvent in vacuo, the product is obtained by distillation, b.p. 71°-74° C. at 0.75 mbar.
With ammonia In aluminum nickel; ethanol 2.a EXAMPLE 2 a) 1-Aminomethylcyclopentane-1-carboxylic acid ethyl ester is obtained by hydrogenating 33 g of 1-cyanocyclopentane-1-carboxylic acid ethyl ester (Alfred Bader Chemicals) in 330 ml of ethanol, which contains approximately 4% ammonia, in the presence of 10 g of Raney nickel at 45° and under normal pressure. After filtering off from the catalyst and removing the solvent in vacuo, the product is obtained by distillation, b.p. 71°-74° at 0.75 mbar.

  • 6
  • [ 110-63-4 ]
  • [ 105-56-6 ]
  • [ 28247-14-5 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene
  • 7
  • [ 110-52-1 ]
  • [ 2999-46-4 ]
  • [ 28247-14-5 ]
YieldReaction ConditionsOperation in experiment
54% With sodium hydride In diethyl ether; dimethyl sulfoxide for 0.333333h; Heating;
  • 8
  • [ 28247-14-5 ]
  • [ 1664-35-3 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In ethanol for 24h; Ambient temperature;
  • 9
  • [ 28247-14-5 ]
  • [ 871022-33-2 ]
YieldReaction ConditionsOperation in experiment
With tri-n-butyltin azide In 1,4-dioxane Heating;
With azido tributyltin (IV) In 1,4-dioxane for 15h; Heating / reflux; 10.1 Step 1. α-cyclopentyltetrazole-5-acetic acid, ethyl ester To a stirred solution of 1-cyano-1-cyclopentanecarboxylic acid, ethyl ester (Bioorg. Med. Chem. Lett. 1999, 9, 369-374.) (6.19 g, 37.0 mmol) in 1,4-dioxane (100 mL) was added nBu3SnN3 (12.3 g, 37.0 mmol) at ambient temperature. The resulting mixture was refluxed for 15 h and concentrated under reduced pressure. To the resulting residue was added 4 M HCl in 1,4-dioxane (50 mL) and concentrated under reduced pressure. The resulting oil was washed twice with hexane to give crude product of the title compound as a yellow oil, which was used for the next step without further purification.
  • 11
  • [ 28247-14-5 ]
  • 1-(<i>tert</i>-butoxycarbonylamino-methyl)-cyclopentanecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / 5 percent Rh/Al2O3
  • 12
  • [ 28247-14-5 ]
  • [ 223763-91-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 87 percent / LiAlH4 / tetrahydrofuran 2: 85 percent / NaOH / tetrahydrofuran
  • 13
  • [ 28247-14-5 ]
  • [ 204514-27-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 87 percent / LiAlH4 / tetrahydrofuran 2: 85 percent / NaOH / tetrahydrofuran 3: 79 percent / aq. NaIO4, RuCl3 / acetonitrile; CCl4 4: 1.) CDI / 2.) THF, reflux 5: Pd(PPh3)4, morpholine / tetrahydrofuran
  • 14
  • [ 28247-14-5 ]
  • [ 204514-16-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 87 percent / LiAlH4 / tetrahydrofuran 2: 85 percent / NaOH / tetrahydrofuran 3: 79 percent / aq. NaIO4, RuCl3 / acetonitrile; CCl4 4: 1.) CDI / 2.) THF, reflux
  • 15
  • [ 28247-14-5 ]
  • [ 457884-62-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 87 percent / LiAlH4 / tetrahydrofuran 2: 85 percent / NaOH / tetrahydrofuran 3: 79 percent / aq. NaIO4, RuCl3 / acetonitrile; CCl4 4: 1.) CDI / 2.) THF, reflux 5: Pd(PPh3)4, morpholine / tetrahydrofuran 6: DCC, DMAP / CH2Cl2 7: TFA 8: 2-hydroxypyridine / toluene 9: m-CPBA / CHCl3 / Ambient temperature
  • 16
  • [ 28247-14-5 ]
  • [ 223763-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 87 percent / LiAlH4 / tetrahydrofuran 2: 85 percent / NaOH / tetrahydrofuran 3: 79 percent / aq. NaIO4, RuCl3 / acetonitrile; CCl4 4: 1.) CDI / 2.) THF, reflux 5: Pd(PPh3)4, morpholine / tetrahydrofuran 6: DCC, DMAP / CH2Cl2 7: TFA 8: 2-hydroxypyridine / toluene
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