Technology Process of 1-chloro-2-(toluene-4-sulfonylamino)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxylic acid methyl ester
There total 14 articles about 1-chloro-2-(toluene-4-sulfonylamino)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene-8-carboxylic acid methyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 15 steps
1: 66 percent / BINAP, NaOBu-t / Pd(DBA)3 / toluene / 80 °C
2: Bu3SnF / Pd(Tol3P)2Cl2 / benzene / Heating
3: H2 / Pd/C / ethyl acetate
4: Et3N / CH2Cl2
5: TBAF / tetrahydrofuran
6: Et3N / CH2Cl2 / 0 °C
7: DBU / 23 °C
8: K2CO3 / methanol; H2O
9: Et3N / CH2Cl2 / 0 °C
10: pyridine
11: p-TSA / Heating
12: 1.) NaHMDS, 2.) PNBSA / 1.) -78 deg C, 2.) -78 deg c to room temperature
13: 1.) 2,2'-(1-methylethylidene)bis(5,5-dimethyl-4,5-dihydrooxazole), copper(I) triflate, 2.) chloranil / 2.) CH2Cl2, 23 deg C
15: MsCl, Et3N
With
pyridine; 2,2'-(1-methylethylidene)bis(5,5-dimethyl-4,5-dihydrooxazole); p-nitrobenzenesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; chloranil; copper(I) triflate; tributyltin fluoride; potassium carbonate; toluene-4-sulfonic acid; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium t-butanolate;
tris-(dibenzylideneacetone)dipalladium(0); palladium on activated charcoal; bis(tris(4-methyl)phenylphosphine)palladium dichloride;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; benzene;
DOI:10.1021/jo990469g
- Guidance literature:
-
Multi-step reaction with 14 steps
1: Bu3SnF / Pd(Tol3P)2Cl2 / benzene / Heating
2: H2 / Pd/C / ethyl acetate
3: Et3N / CH2Cl2
4: TBAF / tetrahydrofuran
5: Et3N / CH2Cl2 / 0 °C
6: DBU / 23 °C
7: K2CO3 / methanol; H2O
8: Et3N / CH2Cl2 / 0 °C
9: pyridine
10: p-TSA / Heating
11: 1.) NaHMDS, 2.) PNBSA / 1.) -78 deg C, 2.) -78 deg c to room temperature
12: 1.) 2,2'-(1-methylethylidene)bis(5,5-dimethyl-4,5-dihydrooxazole), copper(I) triflate, 2.) chloranil / 2.) CH2Cl2, 23 deg C
14: MsCl, Et3N
With
pyridine; 2,2'-(1-methylethylidene)bis(5,5-dimethyl-4,5-dihydrooxazole); p-nitrobenzenesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; chloranil; copper(I) triflate; tributyltin fluoride; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
palladium on activated charcoal; bis(tris(4-methyl)phenylphosphine)palladium dichloride;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1021/jo990469g
- Guidance literature:
-
Multi-step reaction with 13 steps
1: H2 / Pd/C / ethyl acetate
2: Et3N / CH2Cl2
3: TBAF / tetrahydrofuran
4: Et3N / CH2Cl2 / 0 °C
5: DBU / 23 °C
6: K2CO3 / methanol; H2O
7: Et3N / CH2Cl2 / 0 °C
8: pyridine
9: p-TSA / Heating
10: 1.) NaHMDS, 2.) PNBSA / 1.) -78 deg C, 2.) -78 deg c to room temperature
11: 1.) 2,2'-(1-methylethylidene)bis(5,5-dimethyl-4,5-dihydrooxazole), copper(I) triflate, 2.) chloranil / 2.) CH2Cl2, 23 deg C
13: MsCl, Et3N
With
pyridine; 2,2'-(1-methylethylidene)bis(5,5-dimethyl-4,5-dihydrooxazole); p-nitrobenzenesulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; chloranil; copper(I) triflate; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo990469g
