3-(2-(dimethylamino)ethyl)-1H-indol-4-ol [Psilocin]

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27 reactions in Reaxys

2016-06-08 03h:05m:29s (EST)

N OH

1. Query

NH

Search as: As drawn

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NH NH

O N

OH N

Rx-ID: 393275 View in Reaxys 1/27 Yield

Conditions & References

100 %

4.2.3 RRN 82,83,84General procedure for the hydrogenolysis for the synthesis of the natural products General procedure: Psilocin, Bufotenin and Serotonin. To a stirred suspension of the suitable tryptamine (0.25mmol) and an equal weight of 10percent Pd–C in dry methanol (7mL), anhydrous ammonium formate (71mg, 1.125mmol) was added in a single portion under N2. The resulting reaction mixture was stirred at 70°C for 45min. The solution was filtered through a pad of Celite, the solvent was removed under reduce pressure and the residue was purified by flash column chromatography on silica gel (DCM:MeOH 9:1 and 1percent of TEA) to give the corresponding natural product in quantitative yield. With palladium 10 on activated carbon, ammonium formate in methanol, Time= 0.75h, T= 70 °C , Inert atmosphere Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni; Tetrahedron; vol. 72; nb. 18; (2016); p. 2233 - 2238 View in Reaxys

97.0 %

With hydrogen, palladium on activated charcoal in ethanol, Time= 2h, p= 3102.89Torr Nichols, David E.; Frescas, Stewart; Synthesis; nb. 6; (1999); p. 935 - 938 View in Reaxys

84 %

With hydrogen, palladium on activated charcoal in methanol, Time= 1h, T= 20 °C Yamada, Fumio; Tamura, Mayumi; Somei, Masanori; Heterocycles; vol. 49; nb. 1; (1998); p. 451 - 457 View in Reaxys With methanol, aluminum oxide, palladium/alumina, Hydrogenation Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570 View in Reaxys

NH

NH

OH

O O

N

N

Rx-ID: 37741623 View in Reaxys 2/27 Yield

Conditions & References Hydrogenolysis of benzyloxy-derivatives General procedure: To a solution of a compound protected with an O-benzyl group in EtOH, was added 10percent Pd/C (10percent w/w). The mixture was stirred under H2 at a 1 atm pressure for 24 h at room temperature. The mixture was then filtered through Celite and concentrated. With palladium 10 on activated carbon, hydrogen in ethanol, Time= 24h, T= 20 °C , p= 760.051Torr Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 10; (2014); p. 2283 - 2287 View in Reaxys

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NH

NH

O O

OH

O

N

N

O

Rx-ID: 2460925 View in Reaxys 3/27 Yield

Conditions & References

87.5 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887 View in Reaxys

56 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 0.25h, Heating Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179 View in Reaxys Reaction Steps: 2 1: lithium aluminium tetrahydride / tetrahydrofuran / |Reflux 2: palladium 10 on activated carbon; hydrogen / ethanol / 24 h / 20 °C / 760.05 Torr With lithium aluminium tetrahydride, palladium 10 on activated carbon, hydrogen in tetrahydrofuran, ethanol Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 10; (2014); p. 2283 - 2287 View in Reaxys

NH

NH

OH

O

N

N

Rx-ID: 5191370 View in Reaxys 4/27 Yield

Conditions & References

68 %

With boron tribromide in dichloromethane, Time= 9h, T= 20 °C , dealkylation Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135 View in Reaxys

60 %

Stage 1: With boron tribromide in dichloromethane, Time= 9h, T= 20 °C Stage 2: With methanol, potassium hydrogencarbonate in dichloromethane, Time= 0.5h Hu, Chunmei; Qin, Hua; Cui, Yuxin; Jia, Yanxing; Tetrahedron; vol. 65; nb. 45; (2009); p. 9075 - 9080 View in Reaxys

NH

NH

O OH

O

OH N

N

Rx-ID: 5150833 View in Reaxys 5/27 Yield 91 %

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Heating Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660 View in Reaxys

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NH NH

O OH N

Rx-ID: 16302254 View in Reaxys 6/27 Yield

Conditions & References Reaction Steps: 4 1: diethyl ether / 3 h / 5 - 10 °C 2: diethyl ether; CH2Cl2 / 6 h 3: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 4: 97 percent / H2 / 10 percent Pd/C / ethanol / 2 h / 3102.89 Torr With lithium aluminium tetrahydride, hydrogen, palladium on activated charcoal in tetrahydrofuran, 1,4-dioxane, diethyl ether, ethanol, dichloromethane Nichols, David E.; Frescas, Stewart; Synthesis; nb. 6; (1999); p. 935 - 938 View in Reaxys Reaction Steps: 2 1: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate / 48 h / 150 °C / |Inert atmosphere 2: ammonium formate; palladium 10 on activated carbon / methanol / 0.75 h / 70 °C / |Inert atmosphere With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)], palladium 10 on activated carbon, ammonium formate, caesium carbonate in methanol Bartolucci, Silvia; Mari, Michele; Di Gregorio, Giovanni; Piersanti, Giovanni; Tetrahedron; vol. 72; nb. 18; (2016); p. 2233 - 2238 View in Reaxys

NH NH

O O

O

N

OH N

Rx-ID: 16305510 View in Reaxys 7/27 Yield

Conditions & References Reaction Steps: 2 1: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 2: 97 percent / H2 / 10 percent Pd/C / ethanol / 2 h / 3102.89 Torr With lithium aluminium tetrahydride, hydrogen, palladium on activated charcoal in tetrahydrofuran, 1,4-dioxane, ethanol Nichols, David E.; Frescas, Stewart; Synthesis; nb. 6; (1999); p. 935 - 938 View in Reaxys Reaction Steps: 2 1: LiAlH4; dioxane 2: palladium/Al2O3; methanol / Hydrogenation With 1,4-dioxane, methanol, aluminum oxide, palladium/alumina, lithium aluminium tetrahydride Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570 View in Reaxys

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NH NH

O O

O

Cl

OH N

Rx-ID: 16315306 View in Reaxys 8/27 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether; CH2Cl2 / 6 h 2: 94.8 percent / LiAlH4 / tetrahydrofuran; dioxane / 1.) 4 h, 2.) reflux, 20 h 3: 97 percent / H2 / 10 percent Pd/C / ethanol / 2 h / 3102.89 Torr With lithium aluminium tetrahydride, hydrogen, palladium on activated charcoal in tetrahydrofuran, 1,4-dioxane, diethyl ether, ethanol, dichloromethane Nichols, David E.; Frescas, Stewart; Synthesis; nb. 6; (1999); p. 935 - 938 View in Reaxys

NH

NH H 311C

O

I

OH OH

OH

N

HN

11CH

3

Rx-ID: 5050994 View in Reaxys 9/27 Yield

Conditions & References With sodium hydroxide in benzene, Time= 0.166667h, T= 80 °C , Methylation Ametamey; Vollenweider; Patt; Bourquin; Hasler; Beer; Schubiger; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 41; nb. 7; (1998); p. 585 - 594 View in Reaxys

NH

NH O

I

OH

H 13 3 C

OH

OH

N

HN

13CH

3

Rx-ID: 5050998 View in Reaxys 10/27 Yield

Conditions & References With sodium hydroxide in benzene, Time= 0.166667h, T= 80 °C , Methylation Ametamey; Vollenweider; Patt; Bourquin; Hasler; Beer; Schubiger; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 41; nb. 7; (1998); p. 585 - 594 View in Reaxys

NH

NH 2

H

OH

OH N

N

Rx-ID: 5140036 View in Reaxys 11/27 Yield 100 %

Conditions & References With methanol-d4, triethylamine, Time= 48h, Ambient temperature Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660 View in Reaxys

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NH

NH

OH

O

N

O

Rx-ID: 13424157 View in Reaxys 12/27 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether; hexane / cooling 2: 22.0 g / pyridine / tetrahydrofuran / 0.25 h / 20 °C 3: 87.5 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating With pyridine, lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, hexane Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887 View in Reaxys Reaction Steps: 2 1: 1) diethylether, 4 deg C, 18 h 2) diethylether 2: 56 percent / LiAlH4 / tetrahydrofuran / 0.25 h / Heating With lithium aluminium tetrahydride in tetrahydrofuran Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179 View in Reaxys

NH

NH

O O

O

OH N

Cl

O

Rx-ID: 13446574 View in Reaxys 13/27 Yield

Conditions & References Reaction Steps: 2 1: 22.0 g / pyridine / tetrahydrofuran / 0.25 h / 20 °C 2: 87.5 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating With pyridine, lithium aluminium tetrahydride in tetrahydrofuran Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887 View in Reaxys Reaction Steps: 3 1: tetrahydrofuran / 4 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / |Reflux 3: palladium 10 on activated carbon; hydrogen / ethanol / 24 h / 20 °C / 760.05 Torr With lithium aluminium tetrahydride, palladium 10 on activated carbon, hydrogen in tetrahydrofuran, ethanol Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 10; (2014); p. 2283 - 2287 View in Reaxys

NH

NH

OH

OH

N

Rx-ID: 13422684 View in Reaxys 14/27

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Yield

Conditions & References Reaction Steps: 4 1: 34 g / pyridine / CH2Cl2 / 2 h / 20 °C 2: diethyl ether; hexane / cooling 3: 22.0 g / pyridine / tetrahydrofuran / 0.25 h / 20 °C 4: 87.5 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating With pyridine, lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, hexane, dichloromethane Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887 View in Reaxys

NH

3-<2-dimethylamino-ethyl-4-phosphonooxy-indole OH N

Rx-ID: 5453675 View in Reaxys 15/27 Yield

Conditions & References With water, T= 150 °C Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570 View in Reaxys

NH

sodium-salt of 3-<2-dimethylamino-ethyl>-4-phosphonooxy-indole

OH N

Rx-ID: 5453676 View in Reaxys 16/27 Yield

Conditions & References With water, T= 300 - 320 °C Hoffmann et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 1557,1563,1570 View in Reaxys

NH

NH

O OH

O

N

N

Rx-ID: 16307612 View in Reaxys 17/27 Yield

Conditions & References Reaction Steps: 2 1: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating 2: 68 percent / boron tribromide / CH2Cl2 / 9 h / 20 °C With lithium aluminium tetrahydride, boron tribromide in 1,4-dioxane, dichloromethane, 1: Reduction / 2: dealkylation Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135 View in Reaxys

NH

O O

N H

O I

OH N

Rx-ID: 16315818 View in Reaxys 18/27

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Yield

Conditions & References Reaction Steps: 6 1: 271 mg / diisopropylethylamine,; benzyltriethylammonium chloride,; palladium(II) acetate / dimethylformamide / 19 h / 80 °C 2: trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 4: 82 percent / benzene; hexane / 0.83 h / Heating 5: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating 6: 68 percent / boron tribromide / CH2Cl2 / 9 h / 20 °C With lithium aluminium tetrahydride, N-benzyl-N,N,N-triethylammonium chloride, palladium diacetate, boron tribromide, N-ethyl-N,N-diisopropylamine, acetyl chloride, trifluoroacetic acid in 1,4-dioxane, methanol, hexane, dichloromethane, N,N-dimethyl-formamide, benzene, 1: Alkylation / 2: Cyclization / 3: deprotection / 4: amidation / 5: Reduction / 6: dealkylation Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135 View in Reaxys

NH

NH

O O

OH N

O

Rx-ID: 16324786 View in Reaxys 19/27 Yield

Conditions & References Reaction Steps: 3 1: 82 percent / benzene; hexane / 0.83 h / Heating 2: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating 3: 68 percent / boron tribromide / CH2Cl2 / 9 h / 20 °C With lithium aluminium tetrahydride, boron tribromide in 1,4-dioxane, hexane, dichloromethane, benzene, 1: amidation / 2: Reduction / 3: dealkylation Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135 View in Reaxys

O

NH

O

N OH

O O

N

O

Rx-ID: 16328981 View in Reaxys 20/27 Yield

Conditions & References Reaction Steps: 4 1: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 2: 82 percent / benzene; hexane / 0.83 h / Heating 3: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating 4: 68 percent / boron tribromide / CH2Cl2 / 9 h / 20 °C With lithium aluminium tetrahydride, boron tribromide, acetyl chloride in 1,4-dioxane, methanol, hexane, dichloromethane, benzene, 1: deprotection / 2: amidation / 3: Reduction / 4: dealkylation Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135 View in Reaxys

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O

NH

O HN

O OH N

O O O

Rx-ID: 16329225 View in Reaxys 21/27 Yield

Conditions & References Reaction Steps: 5 1: trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 2: 74 percent / acetyl chloride / methanol / 0.5 h / Heating 3: 82 percent / benzene; hexane / 0.83 h / Heating 4: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating 5: 68 percent / boron tribromide / CH2Cl2 / 9 h / 20 °C With lithium aluminium tetrahydride, boron tribromide, acetyl chloride, trifluoroacetic acid in 1,4-dioxane, methanol, hexane, dichloromethane, benzene, 1: Cyclization / 2: deprotection / 3: amidation / 4: Reduction / 5: dealkylation Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 51; nb. 5; (1999); p. 1131 - 1135 View in Reaxys

NH

NH 2H

O OH

OH

O

N

N

Rx-ID: 16437965 View in Reaxys 22/27 Yield

Conditions & References Reaction Steps: 2 1: 91 percent / LiAlH4 / tetrahydrofuran / Heating 2: 100 percent / MeOH-d4, triethylamine / 48 h / Ambient temperature With lithium aluminium tetrahydride, methanol-d4, triethylamine in tetrahydrofuran Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660 View in Reaxys

NH

N

OH

OH

N

Rx-ID: 16464635 View in Reaxys 23/27 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether / 0 °C 3: 91 percent / LiAlH4 / tetrahydrofuran / Heating With lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660 View in Reaxys

NH N 2

H OH

OH

N

Rx-ID: 16464640 View in Reaxys 24/27

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Yield

Conditions & References Reaction Steps: 4 1: diethyl ether / 0 °C 3: 91 percent / LiAlH4 / tetrahydrofuran / Heating 4: 100 percent / MeOH-d4, triethylamine / 48 h / Ambient temperature With lithium aluminium tetrahydride, methanol-d4, triethylamine in tetrahydrofuran, diethyl ether Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660 View in Reaxys

NH

NH

O O

Cl

O

OH

O

Cl

N

O

Rx-ID: 16466046 View in Reaxys 25/27 Yield

Conditions & References Reaction Steps: 2 2: 91 percent / LiAlH4 / tetrahydrofuran / Heating With lithium aluminium tetrahydride in tetrahydrofuran Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660 View in Reaxys

NH

NH 2H

O O

Cl

O

OH

O

Cl

N

O

Rx-ID: 16466050 View in Reaxys 26/27 Yield

Conditions & References Reaction Steps: 3 2: 91 percent / LiAlH4 / tetrahydrofuran / Heating 3: 100 percent / MeOH-d4, triethylamine / 48 h / Ambient temperature With lithium aluminium tetrahydride, methanol-d4, triethylamine in tetrahydrofuran Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 - 660 View in Reaxys

NH

OH N

Rx-ID: 5453674 View in Reaxys 27/27 Yield

Conditions & References Indol V, H2/Pd-Al2O3 Patent; Sandoz Ltd.; US3075992; (1958); ; vol. 61; nb. 5613e; (1964) View in Reaxys 4-Benzyloxy-dimethyltryptamin, Hydrierung an Pd/Al2O3 Patent; Sandoz Ltd.; GB912715; (1958); ; vol. 58; nb. 12516; (1963) View in Reaxys N,N-Dimethyltryptamin, H2O2, <Fe>2+, EDTAH2, Ascorbinsaeure

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Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 275; (1972); p. 613 View in Reaxys N,N-Dimethyltryptamin, H2O2, <Cu>2+, EDTAH2, Ascorbinsaeure Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 275; (1972); p. 613 View in Reaxys N,N-Dimethyltryptamin, O2, <Fe>2+, EDTAH2, Ascorbinsaeure Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 275; (1972); p. 613 View in Reaxys (4-Acetoxy-indolyl-3)-N-dimethylglyoxylamid 11b, LiAlH4 Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283 View in Reaxys der 11b entspr. Hydroxyverb. 11a, LiAlH4 Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283 View in Reaxys 3-(2-Dimethylamino-ethyl)-indol, H2O2 (Ascorbinsaeure, FeSO4, 1,2-Bis(bis-carboxymethyl-amino)-ethan-dinatriumsalz); Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 269; (1969); p. 51 View in Reaxys (yield)3.3 percent Julia; Ricalens; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 269; (1969); p. 51 View in Reaxys Tryptamin (3), H2/Pd Patent; Sandoz; US3078214; (1963); ; vol. 59; nb. 8707a; (1963) View in Reaxys Biosynth. (Aufklaer. mittels Dotier.) Agurell; Nilsson; Tetrahedron letters; vol. 9; (1968); p. 1063 - 1064 View in Reaxys

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