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(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester
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Name

(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester

 EINECS N/A
CAS No. 171489-59-1 Density 1.445
PSA 80.86000 LogP 3.08900
Solubility Chloroform, DMSO, Ethyl Acetate, Methanol Melting Point 230-232 oC
Formula C22H19ClN2O5 Boiling Point 627.5±55.0 °C(Predicted)
Molecular Weight 426.856 Flash Point N/A
Transport Information N/A Appearance Pale Yellow to Pale Orange Solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 171489-59-1 ((1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-2-CHLOROACETYL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE) Hazard Symbols N/A
Synonyms

(1R,3R)-1-(1,3-BENZODIOXOL-5-YL)-2-(CHLOROACETYL)-2,3,4,9-TETRAHYDRO-1H-PYRIDO[3,4-B] INDOLE-3-CARBOXYLIC ACID METHYL ESTER;(6R,12aR)-methyl1,2,3,4-tetrahydro-2-chloroacetyl-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate;(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-B]indole-3-carboxylic acid methyl ester;

Article Data 39

(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester Synthetic route

79-04-9

chloroacetyl chloride

(1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 5 - 20℃; for 1.66667h; Product distribution / selectivity;97%
Stage #1: (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride With triethylamine In tetrahydrofuran; water at 0 - 20℃;
Stage #2: chloroacetyl chloride In tetrahydrofuran; water at 0 - 10℃; for 2h;		95%
With triethylamine In tetrahydrofuran; water at 0 - 10℃; for 2h; Inert atmosphere;93%
79-04-9

chloroacetyl chloride

171596-41-1

(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Stage #1: (1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate With triethylamine In dichloromethane at 20℃; for 0.166667h; Large scale;
Stage #2: chloroacetyl chloride In dichloromethane at 20℃; for 1h; Large scale;		95.2%
With potassium carbonate In dichloromethane; ethyl acetate at 5 - 20℃;94%
With sodium hydrogencarbonate In chloroform at 20℃;93%
120-57-0

piperonal

14907-27-8, 5619-09-0, 7524-52-9, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8

(R)-(+)-tryptophan methyl ester hydrochloride

79-04-9

chloroacetyl chloride

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Stage #1: piperonal; (R)-(+)-tryptophan methyl ester hydrochloride at 85℃; for 3h;
Stage #2: chloroacetyl chloride With triethylamine In tetrahydrofuran; water at 0 - 10℃; for 1h; Product distribution / selectivity;		86%
79-04-9

chloroacetyl chloride

(R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

A

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

B

629652-40-0

(1S,3R)-1-benzo[1,3]dioxol-5-yl-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 2h; N-acyliminium Pictet-Spengler reaction;A 43%
B 34%
120-57-0

piperonal

isooxyurea

isooxyurea

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 23 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C
2: 83 percent / triethylamine / CHCl3 / -10 °C
View Scheme
14907-27-8, 5619-09-0, 7524-52-9, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8

(R)-(+)-tryptophan methyl ester hydrochloride

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 23 percent / trifluoroacetic acid / CH2Cl2 / 24 h / 20 °C
2: 83 percent / triethylamine / CHCl3 / -10 °C
View Scheme
Multi-step reaction with 2 steps
1: 25 percent / TFA / methanol; CH2Cl2 / 60 h / 20 °C
2: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / aq.HCl / methanol / 36 h / Heating
2: 78 percent / NaHCO3 / CH2Cl2; H2O
View Scheme
120-57-0

piperonal

rhodaninoic acid

rhodaninoic acid

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 25 percent / TFA / methanol; CH2Cl2 / 60 h / 20 °C
2: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / aq.HCl / methanol / 36 h / Heating
2: 78 percent / NaHCO3 / CH2Cl2; H2O
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / Et3N; MgSO4 / CH2Cl2 / 24 h
2: 43 percent / DMAP / CH2Cl2 / 2 h / 20 °C
View Scheme
120-57-0

piperonal

glycocoll ester

glycocoll ester

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 42 percent / TFA / CH2Cl2 / 20 °C
2: 93 percent / NaHCO3 / CHCl3 / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: toluene / Heating
2: TFA
3: Et3N
View Scheme
4299-70-1, 7303-49-3, 22032-65-1

D-Tryptophan methyl ester

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 42 percent / TFA / CH2Cl2 / 20 °C
2: 93 percent / NaHCO3 / CHCl3 / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: trifluoroacetic acid / dichloromethane / 24 h / 0 - 20 °C / Molecular sieve
2: triethylamine / chloroform / -10 °C
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water; toluene / 15 h / Reflux; Large scale
2.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Large scale
2.2: 1 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol / 10 h / 70 - 80 °C / Large scale
2: triethylamine / chloroform / 2 h / 20 - 30 °C
View Scheme
749864-17-3

(R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

171489-59-1

methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TFA
2: Et3N
View Scheme

(1R,3R)-1-(1,3-Benzodioxol-5-yl)-2-(chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester Specification

An intermediate in the synthesis of Tadalafil, which is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.

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