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Chemistry
Heterocyclic Building Blocks
Piperidines
quinuclidine
1-Azabicyclo[2.2.2]octane
Chemistry
Material Science
Heterocyclic Building Blocks
Electronic Materials
Piperidines
Other Aliphatic Heterocycles Aliphatic Heterocycles Organic Light-Emitting Diode (OLED) Materials
quinuclidine

[ CAS No. 100-76-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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3d Animation Molecule Structure of 100-76-5
Chemical Structure| 100-76-5
Chemical Structure| 100-76-5
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Quality Control of [ 100-76-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 100-76-5 ]

CAS No. :100-76-5 MDL No. :MFCD00006690
Formula : C7H13N Boiling Point : -
Linear Structure Formula :- InChI Key :SBYHFKPVCBCYGV-UHFFFAOYSA-N
M.W : 111.18 Pubchem ID :7527
Synonyms :

Safety of [ 100-76-5 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P501-P270-P262-P264-P280-P302+P352-P332+P313-P362-P301+P310+P330-P302+P350+P310-P305+P351+P338+P310-P405 UN#:2923
Hazard Statements:H301-H310-H315-H318 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 100-76-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 100-76-5 ]

[ 100-76-5 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 100-76-5 ]
  • [ 74-88-4 ]
  • [ 3618-94-8 ]
YieldReaction ConditionsOperation in experiment
91% In ethyl acetate at 20℃; for 0.166667h;
85% In ethyl acetate at 0℃; for 1h;
65% In ethyl acetate Cooling with ice;
In methanol; acetonitrile at 30℃; ΔH(excit.), ΔS(excit.); various solvent composition;
chemiionization; other alkyl halides and nucleophiles;
With diethyl ether
In acetonitrile
In ethanol at 25℃;
In ethyl acetate
In ethyl acetate
In hexane

Reference： [1]Kazock, Jean-Yves; Taggougui, Mohamed; Carre, Bernard; Willmann, Patrick; Lemordant, Daniel [Synthesis, 2007, # 24, p. 3776 - 3778]
[2]Elias, Shlomi; Karton-Lifshin, Naama; Yehezkel, Lea; Ashkenazi, Nissan; Columbus, Ishay; Zafrani, Yossi [Organic Letters, 2017, vol. 19, # 12, p. 3039 - 3042]
[3]Location in patent: experimental part Wyman, Ian W.; Macartney, Donal H. [Journal of Organic Chemistry, 2009, vol. 74, # 21, p. 8031 - 8038]
[4]Kondo, Yasuhiko; Uematsu, Ryoichi; Nakamura, Yoshinobu; Kusabayashi, Shigekazu [Journal of the Chemical Society. Perkin transactions II, 1988, p. 1219 - 1224]
[5]Yen; Cross; Saunders [Journal of the American Chemical Society, 1991, vol. 113, # 15, p. 5563 - 5565]
[6]Lukes et al. [Collection of Czechoslovak Chemical Communications, 1957, vol. 22, p. 1173,1177]
[7]Kondo, Yasuhiko; Uematsu, Ryoichi; Nakamura, Yoshinobu; Kusabayashi, Shigekazu [Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1988, vol. 84, # 1, p. 111 - 116]
[8]Harmon, Kenneth M.; Southworth, Barbara A. [Journal of Molecular Structure, 1993, vol. 298, p. 23 - 36]
[9]Schalley, Christoph A.; Rivera, Jose M.; Martin, Tomas; Santamaria, Javier; Siuzdak, Gary; Rebek, Julius [European Journal of Organic Chemistry, 1999, # 6, p. 1325 - 1331]
[10]Lledo, Agusti; Rebek Jr., Julius [Chemical Communications, 2010, vol. 46, # 10, p. 1637 - 1639]
[11]Lledo, Agusti; Rebek Jr., Julius [Chemical Communications, 2010, vol. 46, # 45, p. 8630 - 8632]
[12]Karton-Lifshin, Naama; Katalan, Shahaf; Columbus, Ishay; Chen, Ravit; Yehezkel, Lea; Madmon, Moran; Dagan, Shai; Elias, Shlomi; Fridkin, Gil; Zafrani, Yossi [Chemical Communications, 2019, vol. 55, # 83, p. 12471 - 12474]
  • 2
  • [ 622-26-4 ]
  • [ 100-76-5 ]
YieldReaction ConditionsOperation in experiment
70% With silica gel; In water; at 380℃; for 10h;Gas phase; Commercial Exemplified Compound 1 was dissolved in water to prepare a 16 wt% solution. The ceramic backlash ring packed as a catalyst-retaining agent into the quartz reaction tube, after 20cc packed with catalyst 1 obtained in Reference Example 3 in combination, an aqueous solution 0.5 cc/h of Exemplified Compound 1, the nitrogen gas 250 cc/min flow, the reaction was carried out at 380C. Results: The product was analyzed by gas chromatography, is the conversion of 75% Example Compound 1, the reaction yield, Exemplified Compound 5 was 64%. Remove the backlash ring 50cc of the lower catalyst layer in the gas-phase reaction after 10 hours, then heated in a muffle furnace up to 900C was weighed decrease due to the combustion of the deposited tar. A gas phase reaction was carried out according to the method described in Example 1, except that the catalyst 5 obtained in Reference Example 7 was used. As a result of analyzing the product by gas chromatography, the conversion of Exemplified Compound 1 was 91% and the yield of the Exemplified Compound 5 was 70%. Moreover, it was observed weight loss backlash ring in the same manner as in Example 1 was 6.3 g.
Reference： [1]Patent: JP5919803,2016,B2 .Location in patent: Paragraph 0058-0060; 0082
[2]Journal of the American Chemical Society,1952,vol. 74,p. 2894
  • 3
  • [ 3230-23-7 ]
  • [ 56-23-5 ]
  • [ 6457-47-2 ]
  • [ 100-76-5 ]
Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 2806
  • 4
  • [ 3230-23-7 ]
  • [ 6457-47-2 ]
  • [ 100-76-5 ]
Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 2806
  • 5
  • [ 100-76-5 ]
  • [ 75-11-6 ]
  • [ 104304-18-9 ]
YieldReaction ConditionsOperation in experiment
100% In methanol at 28℃; for 2h;
Reference： [1]Almarzoqi, B.; George, A. V.; Isaacs, N. S. [Tetrahedron, 1986, vol. 42, # 2, p. 601 - 608]
  • 6
  • [ 100-76-5 ]
  • [ 6608-47-5 ]
  • [ 39896-06-5 ]
  • 1-Aza-bicyclo[2.2.2]octane; compound with ethenesulfonic acid [ No CAS ]
  • [ 87323-99-7 ]
Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 1977 - 1995
  • 7
  • [ 100-76-5 ]
  • [ 107-36-8 ]
  • [ 87323-99-7 ]
Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 1977 - 1995
  • 8
  • [ 100-76-5 ]
  • [ 33454-82-9 ]
  • [ 122180-10-3 ]
YieldReaction ConditionsOperation in experiment
88% With 5A molecular sieve; fluorine In acetonitrile at -35 - -30℃; for 5.5h;
88% With fluorine In acetonitrile at -35℃; for 5.5h;
Reference： [1]Banks, Ronald Eric; Sharif, Iqbal [Journal of Fluorine Chemistry, 1988, vol. 41, p. 297 - 300]
[2]Banks, Ronald Eric; Sharif Iqbal [Journal of Fluorine Chemistry, 1991, vol. 55, # 2, p. 207 - 214]
  • 9
  • [ 100-76-5 ]
  • [ 100-00-5 ]
  • [ 112473-29-7 ]
YieldReaction ConditionsOperation in experiment
100% In tetrahydrofuran at 50℃; for 75h;
In tetrahydrofuran at 50℃; for 20h; Yield given;
Reference： [1]Ibata, Toshikazu; Isogami, Yasushi; Toyoda, Jiro [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 1, p. 42 - 49]
[2]Ibata, Toshikazu; Isogami, Yasushi; Toyoda, Jiro [Chemistry Letters, 1987, p. 1187 - 1190]
  • 10
  • [ 100-76-5 ]
  • [ 74-95-3 ]
  • [ 104303-96-0 ]
YieldReaction ConditionsOperation in experiment
100% In acetonitrile at 30℃; for 3h;
Reference： [1]Almarzoqi, B.; George, A. V.; Isaacs, N. S. [Tetrahedron, 1986, vol. 42, # 2, p. 601 - 608]
  • 11
  • [ 100-76-5 ]
  • [ 25289-67-2 ]
YieldReaction ConditionsOperation in experiment
100% With dihydrogen peroxide In ethanol at 20℃; for 72h; Cooling with ice;
96% With dihydrogen peroxide In methanol; water at 90℃; for 3h; Sealed tube;
95% With HCFC-225ca,cb; perfluoro-cis-2-n-butyl-3-n-prolyloxaziridine In dichloromethane at -60℃; for 0.333333h;
95% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78 - 20℃;
95% With ozone In diethyl ether for 3h;
95% With ozone In diethyl ether at -78℃; for 3h;
94% With dihydrogen peroxide In acetonitrile at 80℃; for 4.5h;
With dihydrogen peroxide In methanol for 48h;
6.07 g With dihydrogen peroxide In methanol at 0 - 30℃; for 72h;
With 3-chloro-benzenecarboperoxoic acid In chloroform-d1
With 3-chloro-benzenecarboperoxoic acid In chloroform-d1
With dihydrogen peroxide In toluene

Reference： [1]Bender, Dirk; Buss, Sabrina; Giese, Armin; Griesinger, Christian; Herfert, Kristina; Kuebler, Laura; Leonov, Andrei; Linder, Ruth; Maurer, Andreas; Pichler, Bernd J.; Ryazanov, Sergey; Schmidt, Felix; Weckbecker, Daniel [ChemMedChem, 2020]
[2]Escobar, Luis; Escudero-Adán, Eduardo C.; Ballester, Pablo [Angewandte Chemie - International Edition, 2019, vol. 58, # 45, p. 16105 - 16109][Angew. Chem., 2019, vol. 131, # 45, p. 16251 - 16255,5]
[3]Arnone, Alberto; Metrangolo, Pierangelo; Novo, Barbara; Resnati, Giuseppe [Tetrahedron, 1998, vol. 54, # 27, p. 7831 - 7842]
[4]Blades, Kevin; Donohoe, Timothy J.; Winter, Jonathan J. G.; Stemp, Geoffrey [Tetrahedron Letters, 2000, vol. 41, # 24, p. 4701 - 4704]
[5]O'Neil, Ian A.; Bhamra, Inder; Gibbons, Peter D. [Chemical Communications, 2006, # 43, p. 4545 - 4547]
[6]O'Neil, Ian A.; Bhamra, Inder [Tetrahedron Letters, 2009, vol. 50, # 26, p. 3635 - 3638]
[7]Gopiraman, Mayakrishnan; Bang, Hyunsik; Babu, Sundaram Ganesh; Wei, Kai; Karvembu, Ramasamy; Kim, Ick Soo [Catalysis science and technology, 2014, vol. 4, # 7, p. 2099 - 2106]
[8]Srinivas, Shamala; Taylor, K. Grant [Journal of Organic Chemistry, 1990, vol. 55, # 6, p. 1779 - 1786]
[9]Kolb, Hartmuth C.; Andersson, Pher G.; Sharpless, K. Barry [Journal of the American Chemical Society, 1994, vol. 116, # 4, p. 1278 - 1291]
[10]Location in patent: experimental part Pohl, Radek; Dracinsky, Martin; Slavetinska, Lenka; Budesinsky, Milos [Magnetic Resonance in Chemistry, 2011, vol. 49, # 6, p. 320 - 327]
[11]Location in patent: body text Pohl, Radek; Potmischil, Francisc; Dracinsky, Martin; Vanek, Vaclav; Slavetinska, Lenka; Budesinsky, Milos [Magnetic Resonance in Chemistry, 2012, vol. 50, # 6, p. 415 - 423]
[12]Fan, Guang-Meng; Gao, Ji-Xing; Shi, Chao; Yu, Hui; Ye, Le; Jiang, Jia-Ying; Shuai, Cijun; Zhang, Yi; Ye, Heng-Yun [CrystEngComm, 2018, vol. 20, # 44, p. 7058 - 7061]
  • 12
  • [ 100-76-5 ]
  • [ 85282-84-4 ]
YieldReaction ConditionsOperation in experiment
99.7% With bromine In dichloromethane at 0℃; for 0.166667h;
Reference： [1]Blair, Larry K.; Hobbs, Steven; Bagnoli, Nicholas; Husband, Leslie; Badika, Ndofunsu [Journal of Organic Chemistry, 1992, vol. 57, # 5, p. 1600 - 1603]
  • 13
  • [ 100-76-5 ]
  • [ 107969-72-2 ]
  • [ 107957-84-6 ]
  • [ 107957-83-5 ]
YieldReaction ConditionsOperation in experiment
1: 8% 2: 2% 3: 89% With fluorine In trichlorofluoromethane at -78℃;
1: 86% 2: 11% With fluorine In trichlorofluoromethane at -72℃; for 5.5h; Yield given;
1: 11% 2: 86% With fluorine In trichlorofluoromethane at -72℃; for 5.5h;
Reference： [1]Banks, R. E.; Boisson, R. A. Du; Tsiliopoulos, E. [Journal of Fluorine Chemistry, 1986, vol. 32, p. 461 - 466]
[2]Banks, Ronald Eric; Boisson, Richard Arthur Du; Morton, William David; Tsiliopoulos, Efthimios [Journal of the Chemical Society. Perkin transactions I, 1988, p. 2805 - 2812]
[3]Banks, Ronald Eric; Boisson, Richard Arthur Du; Morton, William David; Tsiliopoulos, Efthimios [Journal of the Chemical Society. Perkin transactions I, 1988, p. 2805 - 2812]
  • 14
  • [ 100-76-5 ]
  • [ 107957-84-6 ]
  • [ 107957-83-5 ]
YieldReaction ConditionsOperation in experiment
1: 83% 2: 13% With fluorine In trichlorofluoromethane at -35℃;
Reference： [1]Banks, R. E.; Boisson, R. A. Du; Tsiliopoulos, E. [Journal of Fluorine Chemistry, 1986, vol. 32, p. 461 - 466]
  • 15
  • [ 100-76-5 ]
  • [ 107957-83-5 ]
YieldReaction ConditionsOperation in experiment
86% With trichlorofluoromethane; fluorine at -78℃;
With fluorine at -35℃; for 5h;
Reference： [1]Banks, Ronald Eric; Sharif, Iqbal [Journal of Fluorine Chemistry, 1988, vol. 41, p. 297 - 300]
[2]Banks, R. Eric; Besheesh, Mohamed K. [Journal of Fluorine Chemistry, 1996, vol. 76, # 2, p. 161 - 167]
  • 16
  • [ 100-76-5 ]
  • quinuclidine-2,2,6,6,7,7-d6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% With water-d2 In aq. phosphate buffer at 80℃; for 10h;
With water-d2 at 100℃; for 40h;
Reference： [1]Bhatia, Souful; Spahlinger, Greg; Boukhumseen, Nehal; Boll, Quentin; Li, Zhenglong; Jackson, James E. [European Journal of Organic Chemistry, 2016, vol. 2016, # 24, p. 4230 - 4235]
[2]Dinnocenzo, J. P.; Banach, T. E. [Journal of the American Chemical Society, 1988, vol. 110, # 3, p. 971 - 973]
  • 17
  • [ 100-76-5 ]
  • [ 85282-84-4 ]
YieldReaction ConditionsOperation in experiment
99.6% With bromine In dichloromethane Ambient temperature;
Reference： [1]Blair, Larry K.; Parris, Kevin D.; Hii, Pwo Sen; Brock, Carolyn P. [Journal of the American Chemical Society, 1983, vol. 105, # 11, p. 3649 - 3653]
  • 18
  • [ 100-76-5 ]
  • C14H26N2(1+)*F6Sb(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dioxygenyl hexafluoroantimonate In Chlorodifluoromethane at -140℃; for 4h;
Reference： [1]Dinnocenzo, J. P.; Banach, T. E. [Journal of the American Chemical Society, 1988, vol. 110, # 3, p. 971 - 973]
  • 19
  • [ 100-76-5 ]
  • N-fluoroquinuclidinium hexafluorophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hexaflorophosphate; fluorine In acetonitrile 1.) -35 deg C, 5 h, 2.) r.t.;
Multi-step reaction with 2 steps 1: 69 percent / PF5 / acetonitrile / Ambient temperature 2: 95 percent / F2 / acetonitrile / -35 °C
Reference： [1]Banks, R. Eric; Besheesh, Mohamed K. [Journal of Fluorine Chemistry, 1996, vol. 76, # 2, p. 161 - 167]
[2]Banks, R. Eric; Besheesh, Mohamed K. [Journal of Fluorine Chemistry, 1996, vol. 76, # 2, p. 161 - 167]
  • 20
  • [ 100-76-5 ]
  • [ 1005-56-7 ]
  • O-phenyl 4-(2-chloroethyl)piperidine-1-carbothioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% In dichloromethane at 20℃; for 1h;
95% In dichloromethane at 20℃; for 1h;
Reference： [1]Millan, David S.; Prager, Rolf H. [Tetrahedron Letters, 1998, vol. 39, # 24, p. 4387 - 4390]
[2]Milan, David S.; Prager, Rolf H. [Australian Journal of Chemistry, 1999, vol. 52, # 9, p. 841 - 849]
  • 21
  • [ 3230-23-7 ]
  • [ 56-23-5 ]
  • aqueous sodium hypochlorite [ No CAS ]
  • [ 6457-47-2 ]
  • [ 100-76-5 ]
Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 2806
  • 22
  • [ 100-76-5 ]
  • [ 93-89-0 ]
  • [ 72265-42-0 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: Quinuclidine With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With potassium <i>tert</i>-butylate; sec.-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #3: benzoic acid ethyl ester In tetrahydrofuran at -78 - -30℃; for 1h;
Reference： [1]Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal N.; Singh, Sandeep K. [Chemical Communications, 1999, # 19, p. 1927 - 1928]
  • 23
  • [ 100-76-5 ]
  • [ 90-96-0 ]
  • [ 72265-52-2 ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: Quinuclidine With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With potassium <i>tert</i>-butylate; sec.-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #3: bis(p-methoxyphenyl)methanone In tetrahydrofuran at -78 - -30℃; for 1h;
Reference： [1]Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal N.; Singh, Sandeep K. [Chemical Communications, 1999, # 19, p. 1927 - 1928]
  • 24
  • [ 100-76-5 ]
  • [ 100-52-7 ]
  • erythro-2-(α-hydroxybenzyl)quinuclidine [ No CAS ]
  • (S)-(S)-1-Aza-bicyclo[2.2.2]oct-2-yl-phenyl-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: Quinuclidine With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With potassium <i>tert</i>-butylate; sec.-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #3: benzaldehyde In tetrahydrofuran at -78 - -30℃; for 1h;
Reference： [1]Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal N.; Singh, Sandeep K. [Chemical Communications, 1999, # 19, p. 1927 - 1928]
  • 25
  • [ 100-76-5 ]
  • [ 882-33-7 ]
  • 2-phenylsulfanyl-1-aza-bicyclo[2.2.2]octane [ No CAS ]
  • 2,2-bis-phenylsulfanyl-1-aza-bicyclo[2.2.2]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 52% 2: 4% Stage #1: Quinuclidine With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With potassium <i>tert</i>-butylate; sec.-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #3: diphenyldisulfane In tetrahydrofuran at -78 - -30℃; for 1h;
Reference： [1]Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal N.; Singh, Sandeep K. [Chemical Communications, 1999, # 19, p. 1927 - 1928]
  • 26
  • [ 100-76-5 ]
  • [ 66-77-3 ]
  • erythro-rubanol [ No CAS ]
  • rubanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 41% 2: 15% Stage #1: Quinuclidine With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With potassium <i>tert</i>-butylate; sec.-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #3: 1-naphthaldehyde In tetrahydrofuran at -78 - -30℃; for 1h;
Reference： [1]Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal N.; Singh, Sandeep K. [Chemical Communications, 1999, # 19, p. 1927 - 1928]
  • 27
  • [ 100-76-5 ]
  • [ 66-99-9 ]
  • (R)-(S)-1-Aza-bicyclo[2.2.2]oct-2-yl-naphthalen-2-yl-methanol [ No CAS ]
  • (S)-(S)-1-Aza-bicyclo[2.2.2]oct-2-yl-naphthalen-2-yl-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 40% 2: 24% Stage #1: Quinuclidine With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With potassium <i>tert</i>-butylate; sec.-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #3: β-naphthaldehyde In tetrahydrofuran at -78 - -30℃; for 1h;
Reference： [1]Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal N.; Singh, Sandeep K. [Chemical Communications, 1999, # 19, p. 1927 - 1928]
  • 28
  • [ 100-76-5 ]
  • [ 100-39-0 ]
  • [ 95556-22-2 ]
YieldReaction ConditionsOperation in experiment
34% Stage #1: Quinuclidine With boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: With potassium <i>tert</i>-butylate; sec.-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #3: benzyl bromide In tetrahydrofuran at -78 - -30℃; for 1h;
Reference： [1]Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal N.; Singh, Sandeep K. [Chemical Communications, 1999, # 19, p. 1927 - 1928]
  • 29
  • [ 100-76-5 ]
  • [ 772-03-2 ]
  • N-[2-(2-quinolyl)ethyl]quinuclidinium bromide [ No CAS ]
Reference： [1]Journal of Physical Organic Chemistry,2001,vol. 14,p. 879 - 883
  • 30
  • poly(oxyethylene), telechelic, terminated by tosylate groups [ No CAS ]
  • [ 100-76-5 ]
  • poly(oxyethylene), telechelic, terminated by quinuclidinium tosylate groups [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In toluene at 90℃; for 4h;
Reference： [1]Tezuka, Yasuyuki; Mori, Kazuya; Oike, Hideaki [Macromolecules, 2002, vol. 35, # 14, p. 5707 - 5711]
  • 31
  • [ 100-76-5 ]
  • [ 778-28-9 ]
  • 1-butyl-1-azonia-bicyclo[2.2.2]octane; toluene-4-sulfonate [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 11222 - 11223
  • 32
  • [ 100-76-5 ]
  • [ 1912-32-9 ]
  • 1-butyl-1-azonia-bicyclo[2.2.2]octane; methanesulfonate [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 11222 - 11223
  • 33
  • [ 100-76-5 ]
  • [ 3140-73-6 ]
  • 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-quinuclidinium tetrafluoroborate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With lithium tetrafluoroborate In dichloromethane; acetonitrile at 0℃; for 2h;
70% With lithium tetrafluoroborate In dichloromethane; acetonitrile at 0℃; for 2h;
Reference： [1]Kaminski, Zbigniew J.; Kolesinska, Beata; Kolesinska, Justyna; Sabatino, Giuseppina; Chelli, Mario; Rovero, Paolo; Blaszczyk, Michal; Glowka, Marek L.; Papini, Anna Maria [Journal of the American Chemical Society, 2005, vol. 127, # 48, p. 16912 - 16920]
[2]Olczak; Blaszczyk M; Glowka; Kolesinska; Kaminski [Polish Journal of Chemistry, 2008, vol. 82, # 7, p. 1413 - 1423]
  • 34
  • [ 100-76-5 ]
  • [ 3344-70-5 ]
  • 1,12-bis-(quinuclidinium)dodecane dibromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With triethylamine In various solvent(s) at 100℃; for 48h;
54% In 4-methyl-2-pentanone for 24h; Heating / reflux; 1 To 1,12-dibromododecane (0.50 g, 1.52 mmol) in methyl isobutyl ketone (1 ml) was added quinuclidine (0.34 g, 3.0 mmol). The mixture was deoxygenated by freeze/thaw and stirred at reflux for 24 h, at which time precipitate was formed. The crude mixture was cooled, the precipitate filtered off to yield the desired compound as a white solid (0.45 g, 54 %).'H NMR (200 MHz, CDC13) : 8 3.77-3. 73 (12H, m,), 3.57-3. 48 (4H, m), 2.31-2. 28 (2H, m), 2.22-2. 17 (12H, m), 1.78-1. 74 (4H, m), 1.37-1. 15 (18H, m). 13C NMR (300 MHz, CDC13) : 5 55.2, 28.7, 28. 6,28. 4,24. 4,24. 3,22. 7,2 signals obscured or overlapping; m/z 195 [M-2Br~] 2+ (100%), 470 [M-Br] + (75). Found [M-2Bf] 2+ 195.1979, [C26H5oN2] 2+ requires 195.1982.
Reference： [1]Ng, Clarissa K. L.; Obando, Daniel; Widmer, Fred; Wright, Lesley C.; Sorrell, Tania C.; Jolliffe, Katrina A. [Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 811 - 816]
[2]Current Patent Assignee: UNIVERSITY OF SYDNEY - WO2005/47230, 2005, A1 Location in patent: Page/Page column 36-37
  • 35
  • [ 4677-18-3 ]
  • [ 100-76-5 ]
Reference： [1]Justus Liebigs Annalen der Chemie,1937,vol. 532,p. 80
    Chem.Abstr.,1940,p. 4396
  • 36
  • [ 103260-44-2 ]
  • [ 100-76-5 ]
Reference： [1]Justus Liebigs Annalen der Chemie,1937,vol. 532,p. 80
    Chem.Abstr.,1940,p. 4396
  • 37
  • [ 5344-27-4 ]
  • [ 100-76-5 ]
Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 2894
  • 38
  • [ 1193-65-3 ]
  • [ 100-76-5 ]
YieldReaction ConditionsOperation in experiment
84% With potassium hydroxide; hydrazine In diethylene glycol at 160℃; for 3h;
Multi-step reaction with 3 steps 1: NaOH-solution; Raney nickel; water / 88260.9 Torr / Hydrogenation 2: thionyl chloride / Anschliessend Erwaermen 3: Raney nickel; sodium methylate; methanol / 60 °C / 73550.8 Torr / Hydrogenation
Reference： [1]Kawamata, Yu; Yan, Ming; Liu, Zhiqing; Bao, Deng-Hui; Chen, Jinshan; Starr, Jeremy T.; Baran, Phil S. [Journal of the American Chemical Society, 2017, vol. 139, # 22, p. 7448 - 7451]
[2]Grob et al. [Helvetica Chimica Acta, 1957, vol. 40, p. 2170,2176]
  • 39
  • [ 100-76-5 ]
  • [ 670278-63-4 ]
  • 1-{5-[3-(3,3-dibutyl-7-dimethylamono-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepine-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 50℃; for 22h; 1.p [0247] Step p: Synthesis of 1-{5-[3-(3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenylthiocarbamoyl]-pentyl}-1-azoniabicyclo[2.2.2]octane Bromide [0248] To a solution of 36 mg of the compound obtained in the step o in 1 ml of acetonitrile was added 7 mg of quinuclidine (ta-287 mentioned earlier), and the mixture was heated at 50° C. for 22 hours. The reaction solution was concentrated and the residue was dissolved in 0.2 ml of dichloromethane. 2 ml of ether was added to the solution and the precipitate formed was washed with 2 ml of ether to obtain 32 mg of the title compound. 1H-NMR (CDCl3) δ: 0.84 (3H, t); 0.90 (3H, t); 1.18-1.51 (8H, m); 1.60-2.23 (17H, m); 2.84 (6H, s); 2.95-3.12 (3H, m); 3.26-3.43 (3H, m); 3.58 (6H, t); 6.03-6.07 (2H, m); 6.47 (1H, dd); 7.34-7.39 (2H, m); 7.72-7.76 (1H, m); 7.84 (1H, d); 7.98 (1H, s); 11.56 (1H, s). [0249] MS (m/z): 667 (M+).
In acetonitrile at 50℃; for 22h; 1.p Synthesis of 1-{5-[3-(3,3-dibutyl-7-dimethylamono-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepine-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane bromide (Step p) Synthesis of 1-{5-[3-(3,3-dibutyl-7-dimethylamono-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepine-5-yl)phenylthiocarbamoyl]pentyl}-1-azoniabicyclo[2.2.2]octane bromide Quinuclidine (7 mg, aforementioned ta-287) was added to a solution of 36 mg of the compound obtained at the step o in 1 mL of acetonitrile, and heated at 50°C for 22 hours. The reaction solution was concentrated. The residue was dissolved in 0.2 mL of dichloromethane, and 2 mL of ether was added thereto. The produced precipitate was washed with 2 mL of ether, to yield 32 mg of the title compound. 1H-NMR (CDCl3)δ: 0.84(3H, t); 0.90(3H, t); 1.18-1.51(8H, m); 1.60-2.23(17H, m); 2.84(6H, s); 2.95-3.12(3H, m); 3.26-3.43(3H, m); 3.58(6H, t); 6.03-6.07(2H, m); 6.47(1H, dd); 7.34-7.39(2H, m); 7.72-7.76(1H, m); 7.84(1H, d); 7.98(1H, s); 11.56(1H, s). MS(m/z): 667(M+).
Reference： [1]Current Patent Assignee: ASAHI KASEI CORPORATION - US2005/9805, 2005, A1 Location in patent: Page 126
[2]Current Patent Assignee: ASAHI KASEI CORPORATION - EP1719768, 2006, A1 Location in patent: Example 1
  • 40
  • [ 100-76-5 ]
  • [ 229625-50-7 ]
  • di-tert-butyl N-(phosphonooxymethyl)quinuclidinium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In acetonitrile at 37℃; for 12h; 2.1 Quinuclidine (0.64 mmole) is dissolved in 5 ml of anhydrous acetonitrile. An equal molar amount of chloromethyl di-tert-butyl phosphate is added and the reaction is stirred at 37°C for 12 hours. The reaction is then placed under reduced pressure to remove the solvent at which time 5 ml of anhydrous ethyl ether is added to precipitate the polar product. This suspension is then centrifuged and the supernatant is removed. This process is repeated three times. The solid is then collected and dried to yield 0.487 mmole of protected prodrug (MW 369.6, 78 % yield). 1H NMR (CDCl3, 300MHz) δ 1.54 (s, 18H), 2.07 (m, 6H), 2.27 (m, 1H), 3.86 (t, 6H, J=7.9), 5.36 (d, 2H, J = 8.4). 31P NMR (CDCl3, 500 MHz) δ -14.9704 (t, J=19.5). Mass spectrum (FAB+, GLY) 334 (M+). Melting point 88-105°C.
Reference： [1]Current Patent Assignee: UNIVERSITY OF KANSAS - EP1051181, 2004, B1 Location in patent: Page/Page column 11; 16
  • 41
  • [ 100-76-5 ]
  • [ 2799-73-7 ]
  • [ 864350-21-0 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 50℃; for 19h; 9.a Example 9; 1-(3-{3-[3,3-dibutyl-7-dimethylamino-1,1-dioxo-2,3,4,5-tetrahydro-1,4-benzothiazepin-5-yl)phenyl]thioureido}-propyl)-1-azoniabicyclo[2.2.2]octane Bromide; [0281] Step a: Synthesis of 1-(3-isothiocyanatopropyl)-1-azoniabicyclo-[2.2.2]octane bromide [0282] To a solution of 55 mg of 3-bromopropyl isothiocyanate in 1 ml of acetonitrile was added 33 mg of quinuclidine, and the mixture was heated at 50° C. for 19 hours. The reaction solution was concentrated and the residue was washed 3 times with 1 ml of ether to obtain the title compound.
In acetonitrile at 50℃; for 19h; 9.a Synthesis of 1-(3-isothiocyanatopropyl)-1-azoniabicyclo[2.2.2]octane bromide (Step a) Synthesis of 1-(3-isothiocyanatopropyl)-1-azoniabicyclo[2.2.2]octane bromide Quinuclidine (33 mg) was added to a solution of 55 mg of 3-bromopropyl isothiocyanate in 1 mL of acetonitrile, and heated at 50°C for 19 hours. The reaction solution was concentrated and then a residue was washed three times with 1 mL of ether, to yield the title compound.
Reference： [1]Current Patent Assignee: ASAHI KASEI CORPORATION - US2005/9805, 2005, A1 Location in patent: Page 128
[2]Current Patent Assignee: ASAHI KASEI CORPORATION - EP1719768, 2006, A1 Location in patent: Example 9
  • 42
  • [ 100-76-5 ]
  • [ 847694-38-6 ]
  • 1-{4-[(4-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxy)methyl]benzyl}-1-azoniabicyclo[2.2.2]octane chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In acetonitrile at 20℃; for 5h; 2 Step 2. Preparation 1- {4- [ (4- F (2S, 3R)-1- (4-FLUOROPHENYL)-3- [ (3S)-3- (4- FLUOROPHENYL)-3-HYDROXYPROPYL]-4-OXOAZETIDIN-2-YL} PHENOXY) METHYL] BENZYL}-1- azoniabicyclo [2.2. 2] octane chloride [00102] The product from Step 1 (138. 6 mg, 0. 234 mmol) was dissolved in dry acetonitrile (1.0 mL). Quinuclidine (26.0 mg, 0.234 mmol) in 1.0 mL of dry acetonitrile was added to the bromide mixture and the reaction was stirred at room temperature for 5 h. The solution was concentrated, purified by reverse-phase HPLC (21MM column, 35% to 65% acetonitrile-0. 1% trifluoroacetic acid in water), passed through DOWEX 21K Cl (chloride) anion exchange resin in methanol and concentrated to afford 1-F 4- [ (4- {(2S, (2S, 3R)-l- (4-fluorophenyl)-3- [ (3S)-3- (4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin- 2-yl} phenoxy) methyl] BENZYL}-1-AZONIABICYCLO [2.2. 2] octane chloride (137. 3 mg, 92% yield) as a glassy solid.
Reference： [1]Current Patent Assignee: IRONWOOD PHARMACEUTICALS INC - WO2005/21495, 2005, A2 Location in patent: Page/Page column 44-45
  • 43
  • [ 100-76-5 ]
  • [ 3140-73-6 ]
  • [ 1470-83-3 ]
  • N-(4,6-dimethoxy-2,4,6-triazin-2-yl)-quinuclidinium p-toluenosulphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In acetonitrile at 0℃; for 2h; IV To a mixture of 17.8 g (100 mmol) of lithium p-toluenosulfonate in 30 ml acetonitrile, cooled down to a temperature approximating to 0°C, simultaneously added drop by drop solution of 1.76 g (10 mmol) CDMT in 20 ml of acetonitrile and solution of 1.11 g (10 mmol) of quinuclidine in 5 ml acetonitrile. Then, the stirring of the mixture was continued at a temperature of 0°C for 2 hours, next the precipitate was separated by filtration. The precipitate was washed with 2 portions by 25 ml acetonitrile and the collected filtrates were evaporated to dryness. The residue was washed with ethyl ether and crystallized from acetonitrile. It was obtained 2.95 g of p-toluensulfonate of N-(3,5-dimethoxy-2,4,6-triazinyl-1-)-quinuclidine in the form of thick oily liquid, what equals to 70% yield. The new compound was characterized with the following data: [] Results of elementary analysis of the formula: C19H26N4O5S (422.51) calculated:%C 54.01;%H 6.20;%N 13.26;%S 7.59found:%C 54.04;%H 6.16,%N 13.38,%S 7.22.
Reference： [1]Current Patent Assignee: POLITECHNIKA LODZKA - EP1586566, 2005, A1 Location in patent: Page/Page column 3
  • 44
  • [ 100-76-5 ]
  • [ 1633-83-6 ]
  • C11H21NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 20℃; for 2h; Heating / reflux; 1 Preparation of 4-(azoniabicyclo[2.2.2]oct-2-ylamino)-1-butanesulfonate (Compound LF); To a solution of quinuclidine (1.5 g, 13.5 mmol) in tetrahydrofuran (THF, 15 mL) was added 1,4-butanesultone (2.0 g, 14.4 mmol) at room temperature. The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with THF (2×25 mL) and dried in vacuo. 1H NMR (D2O, 500 MHz) δ ppm 3.26 (m, 6H), 3.02 (m, 2H), 2.82 (t, 2H, J=17.3 Hz), 2.04 (m, 1H), 1.84, (m, 6H), 1.75 (m, 2H), 1.64 (m, 2H). 13C (D2O, 125 MHz) δ ppm 63.68, 54.81, 50.14, 23.51, 21.45, 20.58, 19.19. ES-MS 248 (M+1).
Reference： [1]Current Patent Assignee: BELLUS HEALTH INC. - US2006/223855, 2006, A1 Location in patent: Page/Page column 144
  • 45
  • [ 100-76-5 ]
  • [ 126-83-0 ]
  • 1-(3-sulfo-2-hydroxypropyl)quinuclidinium inner salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Preparation of 1-(3-sulfo-2-hydroxypropyl) quinuclidinium, inner salt (Compound JX); A solution of 3-chloro-2-hydroxy-1-propanesulfonic acid, sodium salt (2 g, 10 mmol) in water (12 mL total volume) was added over 1 hour to a mixture of quinuclidine (1.63 g, 4.7 mmol), water (10 mL) and 1,4-dioxane (10 mL) at 80 C. The mixture was stirred at this temperature for another 2 hours after the end of the addition. The reaction mixture was concentrated then the mixture was passed over a column of Dowex 50×8 (125 g). The fractions containing the pure product were concentrated to a white solid. The solid was dried for 18 hours at 60 C. in the vacuum oven. The desired material was obtained as a white solid (1.92 g, 7.7 mmol, 77%). The 1H and 13C NMR and MS were consistent with the structure.
Reference： [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 145
  • 46
  • [ 100-76-5 ]
  • [ 155863-32-4 ]
  • [ 864350-16-3 ]
YieldReaction ConditionsOperation in experiment
In acetone at 40℃; for 2h; P1.l Synthesis of 1-(4-isothiocyanatobenzyl)-1-azoniabicyclo[2.2.2]octane bromide (Step 1) Synthesis of 1-(4-isothiocyanatobenzyl)-1-azoniabicyclo[2.2.2]octane bromide Quinuclidine (316 mg) (supplied from Aldrich) was added to a solution of 600 mg of the compound obtained at the step k in 19 mL of acetone, and stirred at 40°C for 2 hours. The precipitate therein was collected by filtration, and washed with 10 mL of acetone, to yield 594 mg of the title compound.
Reference： [1]Current Patent Assignee: ASAHI KASEI CORPORATION - EP1719768, 2006, A1 Location in patent: Example P1
  • 47
  • [ 123-75-1 ]
  • [ 100-76-5 ]
  • H13CN [ No CAS ]
  • monocyanophosphonate [ No CAS ]
  • pyrrolidinocyanophosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26.3% With P4O10; hydrogen cyanide In acetonitrile 13 Preparation of Pyrrolidinocyanophosphonate Example 13 Preparation of Pyrrolidinocyanophosphonate Pyrrolidine (0.070 g, 0.99 mmol) was added to 0.95 g of acetonitrile solution of the mixture obtained by reaction of P4O10 (0.85 g, 2.994 mmol), HCN enriched with 10% of H13CN (0.65 mL, 16.85 mmol), and quinuclidine (1.34 g, 12.1 mmol) in 12 mL of CH3CN, at 48° C. for 19 hr (the total weight of the P4O10 reaction mixture, including solvent, after nitrogen purging was 11.10 g). The reaction mixture was heated at 40° C. for 3 hr to give a heterogeneous mixture. The 31P NMR (CD3CN) spectrum shows the presence of two new signals corresponding to pyrrolidinocyanophosphonate (NMR yield, 21.0%) at -15.2 ppm (quintet, 3JPH=5.3 Hz; 1JCP=120.6 Hz, measured on satellite peaks), and monocyanophosphonate (NMR yield, 26.3%) at -17.0 ppm (s; 1JCP=135.8 Hz, measured on satellite peaks). The insoluble fraction in acetonitrile contains monocyanophosphonate.
Reference： [1]Current Patent Assignee: BAYER AG; Monsanto (in: Bayer) - US6218563, 2001, B1
  • 48
  • [ 100-76-5 ]
  • [ 1189-71-5 ]
  • [ 1044409-49-5 ]
  • [ 2039-82-9 ]
  • [ 100306-34-1 ]
  • [ 261621-12-9 ]
  • trans-1,2-cyclohexanediamine [ No CAS ]
  • 1-[4-(4-{(2S,3R)-2-(3'-hydroxybiphenyl-4-yl)-3-[(3S)3-hydroxy-3-phenylpropyl]-4-oxoazetidin-1-yl}phenyl)butyl]-1-azoniabicyclo[2.2.2]octane chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen fluoride; potassium carbonate;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); A quaternary salt is made in the following manner. (3-[tert- butyl(dimethyl)silyl]oxy}phenyl)boronic acid and 4-bromostyrene are coupled under Suzuki conditions with tetrakis(triphenylphosphine)palladium(0) and 2.0 M aqueous potassium carbonate in toluene-ethanol solvent. The product is reacted with chlorosulfonyl isocyanate in ethereal solvent followed by alkali aqueous work-up to generate a beta-lactam. The amide proton is exchanged for an aryl group by reaction with 4-iodophenylcarbonylallyl (generated from the commercially available acid by borane reduction and protected with allyl chloroformate) using trans- 1,2- cyclohexanediamine and copper (T) iodide in decane-dioxane as solvent. Deprotonation of the 3-position of the beta-lactam with a suitable base, such as lithium diisopropylamide, and subsequent quenching with tert-butyl[(lS)-4-iodo-l- phenylbutyl]oxy}dimethylsilane (generated from the commercially available (S)-(-)-3- chloro-1 -phenyl- 1-propanol by protection with tert-butyldimethylchlorosilane and Finkelstein reaction with sodium iodide) provide the 3-substituted intermediate. The allyloxycarbonate protecting group is removed with ammonium formate and tetrakis(triphenylphosphine)palladium(0) in tetrahydrofuran and the resulting alcohol converted into the bromide using carbon tetrabromide and triphenylphosphine in dichloromethane. The silyl protecting groups are removed from the benzyl alcohol EPO <DP n="234"/>and the phenol using 48% hydrofluoric acid in acetonitrile. The resulting compound is reacted with a tertiary amine, such as quinuclidine, purified by HPLC and passed through a chloride ion-exchange column to afford l-[4-(4-{(2S,3R)-2-(3'- hydroxybiphenyl-4-yl)-3 - [(3 S)-3 -hydroxy-3 -phenylpropyl] -4-oxoazetidin- 1 - yl}phenyl)butyl]- 1 -azoniabicyclo[2.2.2]octane chloride.
Reference： [1]Patent: WO2006/124713,2006,A2 .Location in patent: Page/Page column 232-233
  • 49
  • [ 100-76-5 ]
  • [ 75-03-6 ]
  • [ 3618-93-7 ]
YieldReaction ConditionsOperation in experiment
96% In ethyl acetate at 20℃; for 0.5h;
In acetonitrile at 45℃; for 5h;
Reference： [1]Kazock, Jean-Yves; Taggougui, Mohamed; Carre, Bernard; Willmann, Patrick; Lemordant, Daniel [Synthesis, 2007, # 24, p. 3776 - 3778]
[2]Fu, Dongying; He, Yueyue; Hou, Zuoming; Liu, Jun-Chao; Lv, Hui-Peng; Tang, Yuan-Yuan [Chemistry of Materials, 2022, vol. 34, # 7, p. 3518 - 3524]
  • 50
  • [ 100-76-5 ]
  • [ 107-08-4 ]
  • [ 3618-92-6 ]
YieldReaction ConditionsOperation in experiment
86% In ethyl acetate at 20℃; for 1h;
In ethyl acetate
Reference： [1]Kazock, Jean-Yves; Taggougui, Mohamed; Carre, Bernard; Willmann, Patrick; Lemordant, Daniel [Synthesis, 2007, # 24, p. 3776 - 3778]
[2]Berryman, Orion B.; Sather, Aaron C.; Rebek Jr., Julius [Organic Letters, 2011, vol. 13, # 19, p. 5232 - 5235]
  • 51
  • [ 120611-06-5 ]
  • [ 111-78-4 ]
  • [ 100-76-5 ]
  • [ 1295-35-8 ]
Reference： [1]Angewandte Chemie,1989,vol. 101,p. 790 - 792
  • 52
  • [ 100-76-5 ]
  • [ 99589-88-5 ]
  • V(N)Cl2(quin)2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In benzene byproducts: chlorotrimethylsilane; addn. of quinuclidine to a soln. of Cl3V(NSi(CH3)3) and stirring for 30 min; filtration, drying under vacuum, elem. anal.,;
Reference： [1]Critchlow,S.C.; Lerchen,M.E.; Smith,R.C. [Journal of the American Chemical Society, 1988, vol. 110, p. 8071]
  • 53
  • [ 100-76-5 ]
  • Li(tetramethylethylenediamine)BH3(benzyl) [ No CAS ]
  • [ 124287-23-6 ]
YieldReaction ConditionsOperation in experiment
85% With HCl*(C2H5)2O In diethyl ether under N2, dropwise addn. of HCl*Et2O in ether to a soln. of borate in ether at room temp., gas evolution, stirring until gas evolution ceased ( ca. 30 min), addn. of freshly sublimed quinuclidine in ether, heated to reflux for 60 h; filtered in air, evapd., recrystn. from acetone/water;
Reference： [1]Mills, Wyatt J.; Sutton, Christopher H.; Libby, Eduardo; Todd, Lee J. [Inorganic Chemistry, 1990, vol. 29, # 2, p. 302 - 308]
  • 54
  • [ 100-76-5 ]
  • [ 13465-09-3 ]
  • [ 478971-14-1 ]
Reference： [1]Journal of Organometallic Chemistry,2002,vol. 656,p. 203 - 210
  • 55
  • [ 100-76-5 ]
  • indium(I) bromide [ No CAS ]
  • [ 904893-06-7 ]
  • [ 13465-09-3 ]
  • dibromo[carbonyl(η(5)-cyclopentadienyl)nickelo]indium(III), adduct with quinuclidine [ No CAS ]
  • [ 176682-98-7 ]
Reference： [1]Chemische Berichte,1996,vol. 129,p. 297 - 304
  • 56
  • [ 100-76-5 ]
  • [ 15226-74-1 ]
  • indium(I) bromide [ No CAS ]
  • [ 13465-09-3 ]
  • [Co(CO)4InBr2(NC7H13)] [ No CAS ]
Reference： [1]Chemische Berichte,1996,vol. 129,p. 297 - 304
  • 57
  • [ 100-76-5 ]
  • [ 38117-54-3 ]
  • indium(I) bromide [ No CAS ]
  • [ 13465-09-3 ]
  • [Fe(CO)2(C5H5)InBr2(NC7H13)] [ No CAS ]
Reference： [1]Chemische Berichte,1996,vol. 129,p. 297 - 304
  • 58
  • [ 100-76-5 ]
  • [ 1053173-77-5 ]
  • [ 1053173-17-3 ]
YieldReaction ConditionsOperation in experiment
99% In acetonitrile at 25℃; for 16h; 31.B To a solution of acetic acid 1-[4-[4-(4-chloromethyl-benzyloxy)-phenyl]-3-(4-fluoro- phenyl)-2-oxo-oxazolidin-5-yl]-3-phenyl-propyl ester (0.36 g, 0.61 mmol) in MeCN (15 mL) at 25 C was added a solution of quinuclidine (0.067 g, 0.61 mmol). The reaction mixture was stirred at 25 0C for 16 hrs and then was concentrated to provide 1-(4-{4- [5S-(1R-acetoxy-3-phenyl-propyl)-3-(4-fluoro-phenyl)-2-oxo-oxazolidin-4R-yl]- phenoxymethyl}-benzyl)-1-azonia-bicyclo[2.2.2]octane chloride (0.42 g, 99%) as a white foam. 1H-NMR (40 MHz, d-DMSO) δ 7.52-7.41 (m, 6 H), 7.31 (d, 2 H), 7.23 (t, 2 H), 7.16-7.09 (m, 5 H), 6.97 (d, 2 H), 5.52 (d, 1 H), 5.18-5.15 (m, 1 H), 5.05 (s, 2 H), 4.54- 4.51 (m, 1 H), 4.36 (s, 2 H)1 3.37-3.33 (m, 6 H), 2.65-2.53 (m, 2 H), 2.04-1.80 (m, 10 H).
Reference： [1]Current Patent Assignee: PFIZER INC - WO2008/104875, 2008, A1 Location in patent: Page/Page column 60-61
  • 59
  • [ 100-76-5 ]
  • [ 1049636-90-9 ]
  • [ 1049634-55-0 ]
YieldReaction ConditionsOperation in experiment
In chloroform; acetonitrile at 180℃; for 0.5h; Microwave irradiation; 5 Example 5; ^^-((S^-Cyclohexyl-hydroxy-phenyl-methyO-oxazol-S-ylmethylJ-i-azonia- bicyclo[2.2.2]octane bromide; A microwave reaction vessel was charged with [2-((S)-cyclohexyl-hydroxy-phenyl- methyl)-oxazol-5-ylmethyl]-trimethyl-ammonium bromide (20 mg, 0.049 mmol), quinuclidine (55 mg, 0.490 mmol), acetonitrile (0.9 ml_) and chloroform (0.6 ml_). The vessel was sealed and irradiated under microwave heating at 180 0C for 30 min. The reaction was allowed to cool to room temperature. LCMS (Method 2): Rt 2.29 min, m/z 381 [M+].
Reference： [1]Current Patent Assignee: PULMAGEN THERAPEUTICS LLP - WO2008/99186, 2008, A1 Location in patent: Page/Page column 74
  • 60
  • [ 100-76-5 ]
  • [ 123463-20-7 ]
  • C7H13N*C16H26LiNOSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With tert.-butyl lithium In pentane at -90 - 20℃; Inert atmosphere;
Reference： [1]Location in patent: experimental part Ott, Holger; Daeschlein, Christian; Leusser, Dirk; Schildbach, Daniel; Seibel, Timo; Stalke, Dietmar; Strohmann, Carsten [Journal of the American Chemical Society, 2008, vol. 130, # 36, p. 11901 - 11911]
  • 61
  • [ 100-76-5 ]
  • [ 957188-75-9 ]
  • [ 1099795-97-7 ]
YieldReaction ConditionsOperation in experiment
94% In dichloromethane at 0℃; for 1h; Inert atmosphere;
Reference： [1]Ochiai, Masahito; Kawano, Yufuko; Kaneaki, Takao; Tada, Norihiro; Miyamoto, Kazunori [Organic Letters, 2009, vol. 11, # 2, p. 281 - 284]
  • 62
  • [ 100-76-5 ]
  • (3aSR,4RS,8aSR,8bRS)-2-(3-bromopropyl)-4-[5-(5-chloro-2-thienyl)-3-isoxazolyl]hexahydrodipyrrolo[1,2-a:3',4'-c]pyrrole-1,3(2H,4H)-dione [ No CAS ]
  • 1-(3-[(3aSR,4RS,8aSR,8bRS)-4-[5-(5-chloro-2-thienyl)-3-isoxazolyl]-1,3-dioxooctahydrodipyrrolo[1,2-a:3',4'-c]pyrrol-2(3H)-yl]propyl)-1-azoniabicyclo[2.2.2]octane bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In ethanol at 20℃; for 45h;
Reference： [1]Salonen, Laura M.; Bucher, Christoph; Banner, David W.; Haap, Wolfgang; Mary, Jean-Luc; Benz, Joerg; Kuster, Olivier; Seiler, Paul; Schweizer, W. Bernd; Diederich, Francois [Angewandte Chemie - International Edition, 2009, vol. 48, # 4, p. 811 - 814]
  • 63
  • [ 100-76-5 ]
  • [ 13195-50-1 ]
  • [ 127-08-2 ]
  • [ 1173173-98-2 ]
Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 3813 - 3816
  • 64
  • [ 100-76-5 ]
  • [ 540-51-2 ]
  • [ 95177-96-1 ]
YieldReaction ConditionsOperation in experiment
97% In tetrahydrofuran at 50℃; for 5h; 32 l-(2-Hydroxyethyl)quinuclidin-l-ium romide A solution of quinuclidine (2.22 g, 20 mmol) and 2-bromoethanol (1.42 mL, 20 mmol) in 20 mL THF was heated to 50 °C for 5 h. After cooled to room temperature, the solid was filtered and washed with ether to give l-(2-hydroxyethyl)quinuclidin-l-ium bromide as white solid (4.61 g, 97%). NMR (300 MHz, DMSO-i/6) δ 5.24 (/, 1H, J= 4.6 Hz), 3.76-3.83 (m, 2H), 3.46 (t, 6H, J = 7.6 Hz), 3.21 (t, 2H,J= 5.5 Hz), 2.01-2.08 (m, 1H), 1.81-1.88 (m, 6H).
57% In tetrahydrofuran at 50℃; for 4h; Inert atmosphere;
Reference： [1]Current Patent Assignee: MODERNA THERAPEUTICS INC - WO2017/99823, 2017, A1 Location in patent: Page/Page column 308
[2]Location in patent: experimental part Wyman, Ian W.; Macartney, Donal H. [Organic and Biomolecular Chemistry, 2010, vol. 8, # 1, p. 253 - 260]
  • 65
  • [ 100-76-5 ]
  • [ 1259376-12-9 ]
  • [ 1333-74-0 ]
  • C24H11BF15(1-)*H(1+)*C7H13N [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% In toluene at 20℃; for 24h; Autoclave;
Reference： [1]Reddy, J. Sreedhar; Xu, Bao-Hua; Mahdi, Tayseer; Froehlich, Roland; Kehr, Gerald; Stephan, Douglas W.; Erker, Gerhard [Organometallics, 2012, vol. 31, # 15, p. 5638 - 5649]
  • 66
  • [ 100-76-5 ]
  • [ 3140-73-6 ]
  • [ 1421852-26-7 ]
YieldReaction ConditionsOperation in experiment
96% With lithium perchlorate In tetrahydrofuran at 20℃; for 1h;
Reference： [1]Kunishima, Munetaka; Ujigawa, Takae; Nagaoka, Yoshie; Kawachi, Chiho; Hioki, Kazuhito; Shiro, Motoo [Chemistry - A European Journal, 2012, vol. 18, # 49, p. 15856 - 15867]
  • 67
  • [ 100-76-5 ]
  • [ 1940-57-4 ]
  • [ 405113-63-5 ]
YieldReaction ConditionsOperation in experiment
In toluene at 25℃; for 18h; 3 Comparative Example 3Synthesis of 1-fluorenyl-1-azabicyclo[2.2.2]octanium bromide {a photobase generator represented by chemical formula (H3)}; In 250 g of toluene was dissolved 2.4 g of 9-bromofluorene (Tokyo Chemical Industry Co., Ltd.), and 1.2 g of quinuclidine (Aldrich) was added thereto. After a reaction was performed at room temperature (about 25° C.) for 18 hours, the formed solid was collected by filtration, so that 3.0 g of a photobase generator (H3) for comparison (white solid) was obtained. As a result of an analysis by 1H-NMR {300 MHz, DMSO-d6, δ (ppm): 8.0 (d, 2H), 7.9 (d, 2H), 7.6 (t, 2H), 7.4 (t, 2H), 5.7 (s, 1H), 3.5 (t, 6H), 2.0 (m, 1H), 1.9-1.85 (m, 6H)}, it was confirmed that this white solid was 1-fluorenyl-1-azabicyclo[2.2.2]octanium bromide.
Reference： [1]Current Patent Assignee: EVONIK INDUSTRIES AG; SANYO CHEMICAL INDUSTRIES LTD - US8329771, 2012, B2 Location in patent: Page/Page column 40
  • 68
  • [ 100-76-5 ]
  • [ 64-18-6 ]
  • [ 1613621-68-3 ]
  • [ 1613619-58-1 ]
YieldReaction ConditionsOperation in experiment
98 mg Stage #1: Quinuclidine; (R)-5-[2-(3-bromo-propyl)-4-cyano-phenyl]-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester In acetonitrile at 90℃; for 0.5h; Microwave irradiation; Stage #2: formic acid In water; acetonitrile 19 1-(3-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-propyl)-1-azonia-bicyclo[2.2.2]octane formate To a solution of Intermediate 13 (100 mg, 0.17 mmol) in MeCN (2 mL) was added quinuclidine (77 mg, 0.69 mmol). The mixture was heated at 90° C. for 30 mins using microwave irradiation. The solvent was removed in vacuo and the residue was purified by reverse phase chromatography (MDAP), giving the title compound as an off-white solid (98 mg). LC-MS (Method 3): Rt=3.80 min, m/z=607.3 [M]+ 1H NMR (400 MHz, DMSO) δ 11.52 (1H, bs), 8.45 (1H, s), 8.14 (1H, s), 7.97-7.91 (2H, m), 7.87-7.81 (2H, m), 7.73 (1H, dd, J=1.6, 8.2 Hz), 7.67 (1H, bd, J=8.2 Hz), 6.19 (1H, s), 3.54 (3H, s), 3.51-3.43 (6H, m), 3.34-3.22 (3H, m), 2.95 (1H, m), 2.36 (1H, m) 2.17 (3H, s), 2.17 (1H, m) 2.10 (1H, m), 1.93-1.85 (6H, m)
98 mg Stage #1: Quinuclidine; (R)-5-[2-(3-bromo-propyl)-4-cyano-phenyl]-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester In acetonitrile at 90℃; for 0.5h; Microwave irradiation; Stage #2: formic acid 19 Example 19 1-(3-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-propyl)-1-azonia-bicyclo[2.2.2]octane formate To a solution of Intermediate 13 (100 mg, 0.17 mmol) in MeCN (2 mL) was added quinuclidine (77 mg, 0.69 mmol). The mixture was heated at 90°C for 30 mins using microwave irradiation. The solvent was removed in vacuo and the residue was purified by reverse phase chromatography (MDAP), giving the title compound as an off- white solid (98 mg). LC-MS (Method 3): Rt = 3.80 min, m/z = 607.3 [M]+ 1H NMR (400 MHz, DMSO) δ 11.52 (IH, bs), 8.45 (IH, s), 8.14 (IH, s), 7.97-7.91 (2H, m), 7.87-7.81 (2H, m), 7.73 (IH, dd, J = 1.6, 8.2 Hz), 7.67 (IH, bd, J = 8.2Hz), 6.19 (IH, s), 3.54 (3H, s), 3.51-3.43 (6H, m), 3.34-3.22 (3H, m), 2.95 (IH, m), 2.36 (IH, m) 2.17 (3H, s), 2.17 (1H, m) 2.10 (1H, m), 1.93-1.85 (6H, m)
Reference： [1]Current Patent Assignee: Valline SRL - US2014/171414, 2014, A1 Location in patent: Paragraph 0547; 0548; 0549; 0550
[2]Current Patent Assignee: Valline SRL - WO2014/95700, 2014, A1 Location in patent: Page/Page column 84-85
  • 69
  • [ 100-76-5 ]
  • C68H62ClN5O14S2 [ No CAS ]
  • C75H75N6O13S2(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Quinuclidine; C68H62ClN5O14S2 With sodium bromide In N,N-dimethyl acetamide at 15℃; for 3h; Inert atmosphere; Stage #2: With phosphorus tribromide In N,N-dimethyl acetamide; N,N-dimethyl-formamide at -40℃; for 0.5h; 18.7 Step 7: Synthesis of Compound I-18 [0340] After a DMA (1.5 mL) solution of quinuclidine (89 mg, 0.80 mmol) was cooled to 15° C., compound 18k (1.02 g, 0.80 mmol) was added, and the mixture was degassed under reduced pressure. Sodium bromide (165 mg, 1.6 mmol) was added, and, the mixture was stirred at 15° C. for 3 hours. After DMF (3.0 mL) was added, the mixture was cooled to -40° C., phosphorus tribromide (151 μL, 1.6 mmol) was added, and the mixture was stirred at -40° C. for 30 minutes. The reaction mixture was slowly added to an ice-cooled 5% aqueous sodium chloride solution. The precipitated solid was filtered, washed with water, suspended in water, and lyophilized to obtain compound 181 as a brown solid. The resulting compound 181 was used in the next reaction without purification.
Reference： [1]Current Patent Assignee: SHIONOGI & CO., LTD. - US2014/256697, 2014, A1 Location in patent: Paragraph 0340
  • 70
  • [ 100-76-5 ]
  • C54H56ClN7O15S2 [ No CAS ]
  • C61H69N8O14S2(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Quinuclidine; C54H56ClN7O15S2 With sodium bromide In N,N-dimethyl acetamide at 15℃; for 3h; Inert atmosphere; Stage #2: With phosphorus tribromide In N,N-dimethyl acetamide; N,N-dimethyl-formamide at -40℃; for 0.5h; 11.6 Step 6: Synthesis of Compound II-11 [0580] After a DMA (1 mL) solution of quinuclidine (55.6 mg, 0.50 mmol) was cooled to 15° C., compound 11F (571 mg, 0.50 mmol) was added, and the mixture was degassed under reduced pressure. Sodium bromide (103 mg, 1.0 mmol) was added, and the mixture was stirred at 15° C. for 3 hours. After DMF (3.0 mL) was added, the mixture was cooled to -40° C., phosphorus tribromide (94 μL, 1.0 mmol) was added, and the mixture was stirred at -40° C. for 30 minutes. The reaction mixture was slowly added to an ice-cooled 5% aqueous sodium chloride solution. The precipitated solid was filtered, washed with water, suspended in water, and lyophilized to obtain compound 11H as a brown solid. The resulting compound 11H was used in the next reaction without purification.
Reference： [1]Current Patent Assignee: SHIONOGI & CO., LTD. - US2014/256697, 2014, A1 Location in patent: Paragraph 0580
  • 71
  • [ 100-76-5 ]
  • [ 51411-04-2 ]
  • C14H9NO4*C7H13N [ No CAS ]
Reference： [1]CrystEngComm,2013,vol. 15,p. 10470 - 10480
  • 72
  • [ 100-76-5 ]
  • [ 1121-60-4 ]
  • [ 67595-98-6 ]
  • [ 1179-06-2 ]
  • tetrakis(acetonitrile)copper(I) bis(trifluoromethylsulfonyl)imide dichloromethane [ No CAS ]
  • 2Zn(2+)*8Cu(1+)*8C30H24P2*8C2F6NO4S2(1-)*2C68H44N12(2-)*2C7H13N*H2O [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7539 - 7543
    Angew. Chem.,2015,vol. 54,p. 7539 - 7543,5
  • 73
  • [ 100-76-5 ]
  • [ 1121-60-4 ]
  • [ 67595-98-6 ]
  • tetrakis(acetonitrile)copper(I) bis(trifluoromethylsulfonyl)imide dichloromethane [ No CAS ]
  • [ 4129-44-6 ]
  • Zn(2+)*4Cu(1+)*4C36H28P2*C68H44N12(2-)*C7H13N*4C2F6NO4S2(1-) [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 7539 - 7543
    Angew. Chem.,2015,vol. 54,p. 7539 - 7543,5
  • 74
  • [ 100-76-5 ]
  • [ 111-25-1 ]
  • C13H26N(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In ethyl acetate at 20℃; for 96h; ([Quin6]+[Br]-) Freshly-sublimed quinuclidine (9.01 g, 81.0 mmol) and 1-bromohexane (14.08 g, 85.3 mmol, 1.05 eq) were combined in 80 mLof ethyl acetate and stirred at room temperature for 4 days. Theresulting off-white precipitate was filtered, washed with ethyl acetateon a ceramic frit (5 × 25 mL), and dried under vacuum to yield thecorresponding bromide salt in 87% yield. To initiate ion exchange, the bromidesalt ([Quin6]+[Br]-) was dissolved in 100 mL of deionized water followed by the addition of lithium bis(trifluoromethylsulfonyl)imide(1.02 equivalents, pre-dissolved in a minimal amount of water). Thedense lower phase that resulted was extracted with deionized waterseveral times (5 × 100 mL) to exhaustively remove LiBr residues. Theresulting fluid was dried under vacuum at 70 °C for 12 h to yield([Quin6][Tf2N]-) as a colorless free-flowing fluid: 1H NMR (CDCl3,300 MHz): δ 0.88 (t, 3H), 1.34 (m, 6H), 1.66 (m, 2H), 2.02 (m, 6H),2.21 (m, 1H), 3.09 (m, 2H), 3.39 (m, 6H).
Reference： [1]Ayad, Amel; Mutelet, Fabrice; Negadi, Amina; Acree, William E.; Jiang, Bihan; Lu, Amber; Wagle, Durgesh V.; Baker, Gary A. [Journal of Molecular Liquids, 2016, vol. 215, p. 176 - 184]
  • 75
  • [ 100-76-5 ]
  • [ 111-83-1 ]
  • C15H30N(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% In ethyl acetate at 20℃; for 96h; ([Quin8]+[Br]-) Freshly-sublimed quinuclidine (5.16 g, 46.4 mmol) and 1-bromooctane (8.96 g, 46.4 mmol, 1.0 Eq) were combined in 80 mL ofethyl acetate and stirred at room temperature for 4 days. The resultingprecipitate was filtered, washed with ethyl acetate on a ceramic frit(5 × 20 mL), and dried under vacuum to yield the bromide salt in 93%yield. Metathesis was performed in the same manner as for the[Quin6]+ salt described above to yield ([Quin8]+[Tf2N]-): 1H NMR(CDCl3, 300 MHz): δ 0.87 (t, 3H), 1.26-1.31 (m, 10H), 1.66 (m, 2H),2.02 (m, 6H), 2.21 (m, 1H), 3.08 (m, 2H), 3.39 (m, 6H).
Reference： [1]Ayad, Amel; Mutelet, Fabrice; Negadi, Amina; Acree, William E.; Jiang, Bihan; Lu, Amber; Wagle, Durgesh V.; Baker, Gary A. [Journal of Molecular Liquids, 2016, vol. 215, p. 176 - 184]
  • 76
  • [ 100-76-5 ]
  • 2-(2-(2-(3-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)propoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate [ No CAS ]
  • [ 76-05-1 ]
  • 1-(2-(2-(2-(3-(4-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)propoxy)ethoxy)ethoxy)ethyl)-1-azonia-bicyclo[2.2.2]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: Quinuclidine; 2-(2-(2-(3-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)propoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate In butanone at 25℃; Stage #2: trifluoroacetic acid In water; acetonitrile 331 Example 331 Into a 25-mL round-bottom flask, was placed a solution of 2-(2-(2-(3-(4-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)propoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (200 mg, 0.22 mmol, 1.00 equiv) in butanone (2 mL), quinuclidine (5 g, 44.97 mmol, 200.00 equiv). The resulting solution was stirred overnight at 25° C. The resulting mixture was concentrated under vacuum. The crude product (200 mg) was purified by Prep-HPLC with the following conditions (1No.-Pre-HPLC-001(SHIMADZU)): Column, SunFire Prep C18, 19*150 mm 5 um; mobile phase, water with 0.05% TFA and CH3CN (27% CH3CN up to 47% in 6 min, up to 100% in 1 min, down to 27% in 0.7 min); Detector, Waters2545 UvDector 254&220 nm. This resulted in 97.4 mg (52%) of 1-(2-(2-(2-(3-(4-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzyl carbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)propoxy)ethoxy)ethoxy)ethyl)-1-azonia-bicyclo[2.2.2]octane as a yellow semi-solid. LC-MS (ESI, m/z): 831[M+H]+ H-NMR (300 MHz, CD3OD, ppm): δ 8.97 (d, J=3 Hz, 1H), 8.84 (d, J=9 Hz, 1H), 8.45 (s, 1H), 8.16 (s, 1H), 7.91-7.93 (m, 1H), 7.83-7.86 (m, 2H), 7.56-7.73 (m, 5H), 7.51-7.53 (m, 2H), 4.73 (s, 2H), 3.89 (s, 2H), 3.73-3.80 (m, 4H), 3.61-3.66 (m, 8H), 3.49-3.56 (m, 8H), 3.34-3.36 (m, 2H), 2.85 (t, J=9 Hz, 2H), 2.12-2.14 (m, 1H), 1.94-2.01 (m, 8H), 1.25 (t, J=7.2 Hz, 6H).
Reference： [1]Current Patent Assignee: ARDELYX, INC. - US9301951, 2016, B2 Location in patent: Page/Page column 589; 590
  • 77
  • [ 100-76-5 ]
  • 2-isothiocyanatoethyl trifluoromethanesulfonate [ No CAS ]
  • 1-(2-isothiocyanatoethyl)quinuclidinium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.8% In toluene at 20℃; for 8h; 1.42 Synthesis of 1-(2-Isothiocyanatoethyl)quinuclidinium trifluoromethanesulfonate A mixture of 2-isothiocyanatoethyl trifluoromethanesulfonate (78.2 mg, 0.333 mmol) and quinuclidine (37 mg, 1 eq.) in toluene (0.5 mL) was stirred at RT for 8 hrs resulting in a precipitate. The solid was collected by filtration, washed with toluene once and ether twice. The residue was dried in high vacuum to give 104.6 mg (90.8%) as a white solid. MS-ESI: 197.64 (M-OTf-)
Reference： [1]Current Patent Assignee: CLEVELAND CLINIC; PROCTER & GAMBLE CO - US2017/152222, 2017, A1 Location in patent: Paragraph 0204; 0205
  • 78
  • [ 100-76-5 ]
  • 3-isothiocyanatopropyl triflate [ No CAS ]
  • 1-(3-isothiocyanatopropyl)quinuclidinium trifluoromethanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.8% In toluene at 20℃; for 18h; 1.45 Synthesis of 1-(3-Isothiocyanatopropyl) quinuclidinium trifluoromethanesulfonate A mixture of 3-isothiocyanatopropyl trifluoromethanesulfonate (119 mg, 0.476 mmol) and quinuclidine (52.9 mg, 1 eq.) in toluene (0.5 mL) was stirred at RT for 18 hrs resulting in a precipitate. The liquid layer was decanted, the solid was washed with toluene once and ether twice. The residue was dried in high vacuum to give 163 mg (94.8%) as a white solid. MS-ESI: 211.60 (M-OTf-)
Reference： [1]Current Patent Assignee: CLEVELAND CLINIC; PROCTER & GAMBLE CO - US2017/152222, 2017, A1 Location in patent: Paragraph 0210; 0211
  • 79
  • [ 100-76-5 ]
  • [ 615-83-8 ]
  • ethyl 2-(quinuclidinium)valeric acid bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diethyl ether at 10℃; for 504h; To 4 g of quinuclidine dissolved in 25 mL of diethyl ether, 7.52 gof ethyl 2-bromovalerate dissolved in 15 mL of diethyl ether wasslowly dropped on cooling and stirring. The reaction mixture waskept for 3weeks at 10 C, in a refrigerator. The precipitate wasfiltered off and washed with diethyl ether and dried over P2O5, m.p.184e185 C (6.03 g, 53%). 5 g of ethyl 2-(quinuclidinium)-valericacid bromide was dissolved in water (100 mL) and treated with ananion-exchange resin in its basic form (100 g, Amberlite Ira-400),thus hydroxyl ions replaced the bromide ones. After 1 h, whenthe Beilstein test for halide in the water layer was negative, theresin was eluted with water. Removal of water by rotatory evaporatorgave white solid hygroscopic powder of 2-(quinuclidinium)-valerate inner salt, QVa, 3.32 g, 93%; m.p. 223e224 C.
Reference： [1]Dega-Szafran, Zofia; Olejniczak, Anna; Komasa, Anna; Katrusiak, Andrzej; Szafran, Mirosław [Journal of Molecular Structure, 2019, vol. 1180, p. 812 - 825]
  • 80
  • [ 100-76-5 ]
  • [ 29046-78-4 ]
  • (4,4′-di-tert-butyl-2,2′-bipyridine)Ni0(1,5-cyclooctadiene) [ No CAS ]
  • [ 75-05-8 ]
  • [ 72914-19-3 ]
  • 2C50H74Cl2N6Ni2(1+)*2Cl(1-)*7C2H3N [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 89 - 93
  • 81
  • [ 100-76-5 ]
  • [ 1034901-50-2 ]
  • (4,4′-di-tert-butyl-2,2′-bipyridine)Ni0(1,5-cyclooctadiene) [ No CAS ]
  • [ 75-05-8 ]
  • 2C50H74Cl2N6Ni2(1+)*2Cl(1-)*7C2H3N [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 89 - 93
  • 82
  • [ 100-76-5 ]
  • [ 421-14-7 ]
  • N-methylquinuclidin-1-ium trifluoromethoxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In acetonitrile at 20℃; for 48h; Inert atmosphere; Glovebox; Sealed tube;
Reference： [1]Britton, Robert; Friesen, Chadron M.; Jelier, Benson J.; Martin, Rainer E.; Meanwell, Michael; Newton, Josiah J. [Organic Letters, 2020, vol. 22, # 5, p. 1785 - 1790]
  • 83
  • [ 100-76-5 ]
  • [ 88284-48-4 ]
  • [ 1444-94-6 ]
  • 2-(2-(1-phenylpiperidin-4-yl)ethyl)hexahydro-1H-isoindole-1,3(2H)-dione [ No CAS ]
Reference： [1]Advanced synthesis and catalysis,2020
  • 84
  • [ 100-76-5 ]
  • [ 7647-01-0 ]
  • germanium dioxide [ No CAS ]
  • C7H13N*H(1+)*GeCl3(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: hydrogenchloride; germanium dioxide With hypophosphorous acid In water at 74.84℃; for 2h; Stage #2: Quinuclidine In water for 1h;
Reference： [1]Li, Dong; Long, La-Sheng; Ren, Yan-Ping; Zhao, Hai-Xia; Zhao, Xue-Mei; Zheng, Lan-Sun [Inorganic Chemistry, 2020]
  • 85
  • [ 100-76-5 ]
  • [ 402-49-3 ]
  • 1-(4-(trifluoromethyl)benzyl)quinuclidin-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% at 140℃; Sealed tube; Microwave irradiation; 5.1.2. General procedure for the synthesis of the target compounds General procedure: To a prepared solution of 4-Bromobenzyl, 1-(bromomethyl)-4-(trifluoromethyl)benzene or 4-(bromomethyl)-1,10-biphenyl in butanone or acetonitrile as solvent, was added the corresponding intermediates 1-3 and (7-chloro)-4-subtituted quinoline 4 [3,6,7](in a molar ratio of 1:1). The reaction was performed in a sealed tube a under microwave irradiation (140 °C, 28-33 min). Target compounds a-v were isolated after chromatography flash purification or simple filtration and wash with diethyl ether.
Reference： [1]Serrán- Aguilera, Lucía; Mariotto, Elena; Rubbini, Gianluca; Castro Navas, Francisco Fermín; Marco, Carmen; Carrasco-Jiménez, María Paz; Ballarotto, Marco; Macchiarulo, Antonio; Hurtado-Guerrero, Ramón; Viola, Giampietro; Lopez-Cara, Luisa Carlota [European Journal of Medicinal Chemistry, 2020, vol. 207]
  • 86
  • [ 100-76-5 ]
  • [ 2567-29-5 ]
  • 1-([1,1'-biphenyl]-4-ylmethyl)quinuclidin-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% at 140℃; Sealed tube; Microwave irradiation; 5.1.2. General procedure for the synthesis of the target compounds General procedure: To a prepared solution of 4-Bromobenzyl, 1-(bromomethyl)-4-(trifluoromethyl)benzene or 4-(bromomethyl)-1,10-biphenyl in butanone or acetonitrile as solvent, was added the corresponding intermediates 1-3 and (7-chloro)-4-subtituted quinoline 4 [3,6,7](in a molar ratio of 1:1). The reaction was performed in a sealed tube a under microwave irradiation (140 °C, 28-33 min). Target compounds a-v were isolated after chromatography flash purification or simple filtration and wash with diethyl ether.
Reference： [1]Serrán- Aguilera, Lucía; Mariotto, Elena; Rubbini, Gianluca; Castro Navas, Francisco Fermín; Marco, Carmen; Carrasco-Jiménez, María Paz; Ballarotto, Marco; Macchiarulo, Antonio; Hurtado-Guerrero, Ramón; Viola, Giampietro; Lopez-Cara, Luisa Carlota [European Journal of Medicinal Chemistry, 2020, vol. 207]
  • 87
  • [ 100-76-5 ]
  • [ 16940-66-2 ]
  • [ 25605-09-8 ]
YieldReaction ConditionsOperation in experiment
99% With carbon dioxide In tetrahydrofuran at 20℃; for 1h;
Reference： [1]Hamann, Henry J.; Lin, Randy; Veeraraghavan Ramachandran, P. [Dalton Transactions, 2021, vol. 50, # 45, p. 16770 - 16774]
  • 88
  • [ 100-76-5 ]
  • C11H10ClN3O2 [ No CAS ]
  • C18H23N4O2(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
34.6% In tetrahydrofuran at 20℃; for 0.5h; 1 Compound 4: 4-(4,6-bis(3-alkynyl-1-oxy)-1,3,5-triazin-2-yl)-4-methylmorpholin-4-amine hydrochloride preparation General procedure: 2,4-bis(3-alkynyl-1-oxy)-6-chloro-1,3,5-triazine (100 mg, 0.4 mmol) and 2 mL of tetrahydrofuran were added to a 50 mL reaction flask and dissolved under stirring,N-methylmorpholine (74 mg, 0.8 mmol) was slowly added dropwise with stirring,The reaction was stirred at room temperature for 30 min, and a white solid was precipitated. filter,The solid was rinsed twice with THF and dried to give 4-(4,6-bis(3-ynyl-1-oxy)-1,3,5-triazin-2-yl)-4-methylmorpholine 110 mg of -4-amine hydrochloride, the yield was 87.3%.
Reference： [1]Current Patent Assignee: OCEAN UNIV CHINA - CN114560819, 2022, A Location in patent: Paragraph 0040; 0044-0046; 0051

Tags: 100-76-5 synthesis path| 100-76-5 SDS| 100-76-5 COA| 100-76-5 purity| 100-76-5 application| 100-76-5 NMR| 100-76-5 COA| 100-76-5 structure

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quinuclidine
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Material Science
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