(+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

Base Information

Chemical Name:(+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate
CAS No.:1218918-64-9
Molecular Formula:C₂₂H₂₃FN₂O₅S
Molecular Weight:446.499
Hs Code.:

Synonyms:(+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

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Chemical Property of (+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

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Technology Process of (+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

There total 16 articles about (+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

: (+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(oxo)acetate

: 1218918-64-9
(+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1016/j.bmcl.2011.03.085

Reference yield:

: 1H-2-indolepropenoic acid ethyl ester

: 1218918-64-9
(+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

Guidance literature:: Multi-step reaction with 13 steps

1: caesium carbonate / N,N-dimethyl-formamide / 18 h / 60 °C

2: palladium on carbon; hydrogen / ethanol / 12 h / 760.05 Torr

3: potassium tert-butylate / tetrahydrofuran / 20 h / 20 °C

4: silica gel / toluene / 2 h / Reflux

5: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

6: triethylamine / dichloromethane / 0.5 h / -40 °C

7: sodium azide / N,N-dimethyl-formamide / 12 h / 60 °C

8: palladium on carbon; hydrogen / methanol / 12 h / 20 °C

9: dmap; triethylamine / dichloromethane / 4 h / 20 °C

10: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

11: dichloromethane / 1 h / 0 °C

12: dichloromethane / 1 h / 20 °C

13: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

With dmap; sodium tetrahydroborate; sodium azide; palladium on carbon; potassium tert-butylate; hydrogen; silica gel; sodium hydride; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Dieckmann reaction;
DOI:10.1016/j.bmcl.2011.03.085

Reference yield:

: 24621-70-3
2-(hydroxymethyl)indole

: 1218918-64-9
(+/-)-methyl {7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-10-yl}(hydroxy)acetate

Guidance literature:: Multi-step reaction with 15 steps

1: manganese(IV) oxide / dichloromethane / 3 h / 20 °C

2: dichloromethane / 12 h / 20 °C

3: caesium carbonate / N,N-dimethyl-formamide / 18 h / 60 °C

4: palladium on carbon; hydrogen / ethanol / 12 h / 760.05 Torr

5: potassium tert-butylate / tetrahydrofuran / 20 h / 20 °C

6: silica gel / toluene / 2 h / Reflux

7: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

8: triethylamine / dichloromethane / 0.5 h / -40 °C

9: sodium azide / N,N-dimethyl-formamide / 12 h / 60 °C

10: palladium on carbon; hydrogen / methanol / 12 h / 20 °C

11: dmap; triethylamine / dichloromethane / 4 h / 20 °C

12: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C

13: dichloromethane / 1 h / 0 °C

14: dichloromethane / 1 h / 20 °C

15: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C

With dmap; manganese(IV) oxide; sodium tetrahydroborate; sodium azide; palladium on carbon; potassium tert-butylate; hydrogen; silica gel; sodium hydride; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Wittig reaction / 5: Dieckmann reaction;
DOI:10.1016/j.bmcl.2011.03.085