Products Categories
CAS No.: | 171489-59-1 |
---|---|
Name: | (1R,3R)-METHYL-1,2,3,4-TETRAHYDRO-2-CHLOROACETYL-1-(3,4-METHYLENEDIOXYPHENYL)-9H-PYRIDO[3,4-B]INDOLE-3-CARBOXYLATE |
Article Data: | 39 |
Molecular Structure: | |
Formula: | C22H19ClN2O5 |
Molecular Weight: | 426.856 |
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; |
Density: | 1.445 |
Melting Point: | 230-232 oC |
Boiling Point: | 627.5±55.0 °C(Predicted) |
Solubility: | Chloroform, DMSO, Ethyl Acetate, Methanol |
Appearance: | Pale Yellow to Pale Orange Solid |
PSA: | 80.86000 |
LogP: | 3.08900 |
chloroacetyl chloride
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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% |
chloroacetyl chloride
(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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% |
piperonal
(R)-(+)-tryptophan methyl ester hydrochloride
chloroacetyl chloride
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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% |
chloroacetyl chloride
A
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
B
(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 | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 2h; N-acyliminium Pictet-Spengler reaction; | A 43% B 34% |
piperonal
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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 |
(R)-(+)-tryptophan methyl ester hydrochloride
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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 |
piperonal
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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 |
piperonal
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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 |
D-Tryptophan methyl ester
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
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 |
(R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA 2: Et3N View Scheme |
What can I do for you?
Get Best Price
An intermediate in the synthesis of Tadalafil, which is used for the treatment of erectile dysfunction. A phosphodiesterase 5 inhibitor.