(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 supplier

Name
(1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-2-CHLOROACETYL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE
EINECS
CAS No. 171489-59-1
Article Data39
CAS DataBase
Density 1.445
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
Transport Information
Appearance Pale Yellow to Pale Orange Solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 80.86000
LogP 3.08900

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 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

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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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

Conditions	Yield
With triethylamine In tetrahydrofuran Reflux;

: 120-57-0
piperonal

: 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

Conditions	Yield
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: 0.25 h / 110 °C 2: triethylamine / water; tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 0.25 h / 110 °C 2: triethylamine / tetrahydrofuran; water / 2 h / 0 - 10 °C / Inert atmosphere View Scheme

: 1039484-71-3
(3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahidro-9H-pyrido[3,4-b]indole-3-carboxylic acid methyl ester

: 79-04-9
chloroacetyl chloride

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

Conditions	Yield
With triethylamine In dichloromethane

...Expand

: 153-94-6
D-tryptophan

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 4 h / 40 °C 2.1: carbonic acid dimethyl ester / 18 h / Reflux 3.1: triethylamine / 1 h / Ionic liquid 3.2: 0 °C / Ionic liquid View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1.5 h / 0 - 68 °C 2.1: isopropyl alcohol / 66 - 70 °C 3.1: triethylamine / tetrahydrofuran / 0 °C 3.2: 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 2 h / Reflux; Large scale 2.1: hydrogenchloride / water; toluene / 15 h / Reflux; Large scale 3.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Large scale 3.2: 1 h / 20 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / 2 h / 10 - 45 °C / Large scale 2: isopropyl alcohol / 10 h / 70 - 80 °C / Large scale 3: triethylamine / chloroform / 2 h / 20 - 30 °C View Scheme

: (3R)-1-(3,4-methylenedioxyphenyl)-1,2,3,4-tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid 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

Conditions	Yield
With sodium carbonate In water; acetonitrile at 5 - 10℃; Temperature; Solvent;	13.4 g

: 495-76-1
piperonol

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane / 20 °C 2: isopropyl alcohol / Reflux 3: triethylamine / tetrahydrofuran / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 2: isopropyl alcohol / 24 h / Reflux 3: triethylamine / dichloromethane / -10 °C View Scheme
Multi-step reaction with 3 steps 1.1: aluminum isopropoxide / toluene / 110 °C 1.2: 2 h / Heating / reflux 2.1: isopropyl alcohol / 66 - 70 °C 3.1: triethylamine / tetrahydrofuran / 0 °C 3.2: 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane / 20 °C 2: isopropyl alcohol / 80 - 100 °C 3: triethylamine / dichloromethane / 3 h / 0 - 20 °C View Scheme

: C14H13ClN2O4

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluorormethanesulfonic acid / dichloromethane / 3 h / 20 °C 2.1: dichloromethane / 5 h / 30 °C 2.2: 6 h / 75 - 80 °C / 22502.3 Torr 3.1: sodium hydroxide / dichloromethane / 2 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1.1: trifluorormethanesulfonic acid / dichloromethane / 3 h / 20 °C 2.1: ethyl acetate / 5 h / 30 °C 2.2: 6 h / 75 - 80 °C / 22502.3 Torr / Inert atmosphere 3.1: sodium hydroxide / dichloromethane / 2 h / 0 - 5 °C View Scheme

: C13H12N2O3

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ethyl acetate / 5 h / 30 °C 1.2: 6 h / 75 - 80 °C / 22502.3 Torr / Inert atmosphere 2.1: sodium hydroxide / dichloromethane / 2 h / 0 - 5 °C View Scheme

: 74-89-5
methylamine

: 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

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide at 20℃;	95%
In N,N-dimethyl-formamide at 20℃; for 10h;	95%
In methanol for 3h; Reflux; Large scale;	95.3%

: 74-89-5
methylamine

: 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

: 171596-27-3
(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In ethanol; water at 40℃; for 4h;	95%

: 74-89-5
methylamine

: 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

: (6R, 12aR)-2, 3, 6, 7, 12, 12a-hexahydro-2-methyl-6-(3, 4-methylenedioxyphenyl)-pyrazino-[2',1':6,1] pyrido [3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Stage #1: methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate In tetrahydrofuran at 30 - 55℃; for 1h; Stage #2: methylamine In tetrahydrofuran at 5 - 55℃; for 1h;	94.6%

: 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

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With methylamine In dichloromethane for 2h;	93.5%
With methylamine In water for 20h; Ionic liquid;	355 mg

: 103-67-3
benzyl-methyl-amine

: 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

: 1224724-00-8
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-(2-(benzyl(methyl)amino)acetyl)-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In ISOPROPYLAMIDE at 20℃; for 2h; Product distribution / selectivity;	90%

: 35303-76-5
4-(2-aminoethyl)benzenesulfonamide

: 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

: 4-[2-((6R,12aR)-6-benzo[1,3]dioxol-5-yl-1,4-dioxo-3,4,6,7,12,12a-hexahydro-1H-pyrazino-[1',2':1,6]pyrido[3,4-b]indol-2-yl)ethyl]-benzenesulfonamide

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 45℃; for 22h;	89.5%

: 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

: (6R,12aR)-2-amino-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With hydrazine In tetrahydrofuran; methanol; water at 20℃; for 108h;	82%

: 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

: 6-(benzo[d][1,3]dioxol-5-yl)-2-(piperidin-4-ylmethyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With tert-butyl 4-(aminomethyl)piperidine-1-carboxylate In methanol at 80℃;	79%

: 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

: 171596-36-4
(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With ammonia In methanol at 45℃; for 20h;	70%
With ammonia In methanol at 40℃; for 72h;	68%
With ammonia In methanol Reflux;	60%
With ammonia Heating;	31%

: 74-89-5
methylamine

: 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

: C22H21N3O5

Conditions

Conditions	Yield
In water; acetonitrile at 90℃; for 2h; Temperature; Solvent;	69.88%

: 75-31-0
isopropylamine

: 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

: (6R,12aR)-6-(benzo(d)[1,3]dioxol-5-yl)-2-isopropyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In methanol Heating;	69%

: 86945-25-7
4-(2-aminoethyl)-1-(phenylmethyl)piperidine

: 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

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-(2-(1-benzylpiperidin-4-yl)ethyl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	67%
With triethylamine In methanol for 18h; Reflux;	67%

: 924-44-7
glyoxylic acid ethyl 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

: methyl-(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-9-((R)-2-ethoxy-1-hydroxy-2-oxoethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Conditions

Conditions	Yield
With C53H43O4PSi2 In diethyl ether; toluene at 0℃; for 48h; enantioselective reaction;	67%

: 5470-11-1
hydroxylamine 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

: (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-hydroxy-6-(3,4-methylendioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 45℃; for 24h;	66%

: 50541-93-0
4-amino-1-benzylpiperidine

: 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

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-(1-benzylpiperidin-4-yl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	65%
In ethanol Reflux;	59%
In ethanol at 50℃;

: 2038-03-1
4-(2-AMINOETHYL)MORPHOLINE

: 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

: (6R,12AR)-6-benzo[1,3]dioxol-5-yl-2-(2-morpholin-4-ylethyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	62%
In ethanol Reflux;	39%
In ethanol at 50℃;

: 51-67-2
tyrosamine

: 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

: 1295647-19-6
(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-[2-(4-hydroxyphenyl)ethyl]-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido-[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In ethanol Reflux;	62%

: 18471-40-4, 60652-45-1, 114715-38-7, 114715-39-8
1-Benzyl-3-aminopyrrolidine

: 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

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-(1-benzylpyrrolidin-3-yl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	59%

: 88915-26-8
4-aminomethyl-1-benzylpiperidine

: 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

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-((1-benzylpiperidin-4-yl)methyl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	58%

: 109-73-9
N-butylamine

: 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

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-butyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In methanol Heating;	57%
In ethanol Reflux;	44%

: 1106986-47-3
4-morpholinobenzylamine 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

: 1295647-20-9
(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-(4-morpholin-4-ylbenzyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido-[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Microwave irradiation;	57%

: 114715-39-8
(R)-1-benzyl-3-aminopyrrolidine

: 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

: 574730-01-1
(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-((R)-1-benzylpyrrolidin-3-yl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	56%
Reflux;	48%
Stage #1: (R)-1-benzyl-3-aminopyrrolidine; methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate for 12 - 24h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate	48%
In ethanol at 50℃;

: 934-98-5
2-(4-methylpiperazin-1-yl)ethylamine

: 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

: (6R,12AR)-6-benzo[1,3]dioxol-5-yl-2-[2-(4-methylpiperazin-1-yl)ethyl]-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	56%

: 7803-57-8
hydrazine hydrate

: 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

: (6R,12aR)-2-amino-6-(benzo[d][1,3]dioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In ethanol Microwave irradiation;	56%

: 25842-32-4
1-(2-aminoethyl)-4-benzylpiperidine

: 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

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-(2-(4-benzylpiperidin-1-yl)ethyl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	56%

: 1425498-90-3
5-((7-methoxynaphthalen-1-yl)methyl)-1H-tetrazole

: 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

: 1-benzo[1,3]dioxol-5-yl-2-{2-[5-(7-methoxy-naphthalen-1-ylmethyl)-tetrazol-2-yl]acetyl}-2,3,4,9-tetrahydro-1H-[b]-carboline-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃;	55%

: 1664-39-7
N-methyl-N-phenylethylenediamine

: 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

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-(2-(methyl(phenyl)amino)ethyl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido-[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;	55%

(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.

Product Name

(1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-2-CHLOROACETYL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE

Synthetic route

(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

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