TROPARIL

Query 1. Query

Query

Results

Date

RX.PXRN=5480750

6 reactions in Reaxys

2018-07-07 15h:37m:44s (UTC)

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1/4

2018-07-07 15:38:21

N N

Br

Mg

O O

O O

Rx-ID: 8521425 View in Reaxys 1/6 Yield

Conditions & References Stage 1: in diethyl ether, T= -49 °C , Addition Stage 2: With trifluoroacetic acid, T= -78 °C , Hydrolysis Sandell; Helfenbein; Halldin; Chou; Emond; Guilloteau; Farde; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 42; nb. SUPPL. 1; (1999); p. S51-S53 View in Reaxys in diethyl ether, Addition Sandell, Johan; Halldin, Christer; Helfenbein, Julie; Chou, Yuan-Hwa; Vercouillce, Johnny; Emond, Patrick; Swahn, Carl-Gunnar; Guilloteau, Denis; Farde, Lars; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 43; nb. 10; (2000); p. 1033 - 1046 View in Reaxys 1.a Stage 1: in diethyl ether, Time= 3h, T= -40 °C Stage 2: With trifluoroacetic acid in diethyl ether, Time= 1h, T= -80 °C Patent; ORPHACHEM; WO2008/59349; (2008); (A1) English View in Reaxys in diethyl ether Gu, Xiao-Hui; Zong, Rushi; Kula, Nora S.; Baldessarini, Ross J.; Neumeyer, John L.; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 23; (2001); p. 3049 - 3053 View in Reaxys Stage 1: With copper(l) iodide in tetrahydrofuran, Time= 0.5h, T= 0 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 5h, T= -43 - -40 °C , Inert atmosphere Stage 3: With trifluoroacetic acid in tetrahydrofuran, dichloromethane, Time= 0.5h, T= -78 °C , Inert atmosphere, stereoselective reaction Riss, Patrick Johannes; Hummerich, Rene; Schloss, Patrick; Organic and Biomolecular Chemistry; vol. 7; nb. 13; (2009); p.

2688 - 2698 View in Reaxys in diethyl ether, dichloromethane Riss, Patrick J.; Hooker, Jacob M.; Alexoff, David; Kim, Sung-Won; Fowler, Joanna S.; Roesch, Frank; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 15; (2009); p. 4343 - 4345 View in Reaxys

N

Br

Mg

O O

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

2/4

2018-07-07 15:38:21

N

N

O

O

O

O

Rx-ID: 4660739 View in Reaxys 2/6 Yield

Conditions & References

14 %

in diethyl ether, dichloromethane, Time= 3.5h, T= -40 °C Xu; Trudell; Journal of Heterocyclic Chemistry; vol. 33; nb. 6; (1996); p. 2037 - 2039 View in Reaxys Stage 1: in diethyl ether, T= -40 °C , Addition Stage 2: With trifluoroacetic acid in diethyl ether, T= -78 °C , Hydrolysis Tamiz, Amir P.; Smith, Miles P.; Kozikowski, Alan P.; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 3; (2000); p.

297 - 300 View in Reaxys

O

N N

O

O O

O

O

Rx-ID: 15755388 View in Reaxys 3/6 Yield

Conditions & References Reaction Steps: 2 1.1: 2M aq. HCl / Heating 1.2: POCl3 / Heating 1.3: MeOH / -40 °C 2.1: diethyl ether / -40 °C 2.2: TFA / diethyl ether / -78 °C With hydrogenchloride in diethyl ether, 1.1: Hydrolysis / 1.2: Chlorination / 1.3: Elimination / 2.1: Addition / 2.2: Hydrolysis Tamiz, Amir P.; Smith, Miles P.; Kozikowski, Alan P.; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 3; (2000); p.

297 - 300 View in Reaxys

N

Br

Mg

O O

N

N

O O

O O

Rx-ID: 8965915 View in Reaxys 4/6

Copyright © 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Yield

Conditions & References in diethyl ether, Time= 3h, T= -20 °C Chung, Kyoo-Hyun; Lim, Choong Hwan; Lee, Dong Reyoul; Jin, Changbae; Chi, Dae Yoon; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 23; (2001); p. 3077 - 3080 View in Reaxys

N N Li

O O

O O

Rx-ID: 29235755 View in Reaxys 5/6 Yield

Conditions & References Riss, Patrick J.; Hooker, Jacob M.; Alexoff, David; Kim, Sung-Won; Fowler, Joanna S.; Roesch, Frank; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 15; (2009); p. 4343 - 4345 View in Reaxys

N

O O

Rx-ID: 22896637 View in Reaxys 6/6 Yield

Conditions & References 9.a Patent; Georgetown University; US6350758; (2002); (B1) English View in Reaxys

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