(4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Base Information

• Chemical Name: (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate
• CAS No.: 2098497-32-4
• Molecular Formula: C₁₇H₂₂BrN₃O₃
• Molecular Weight: 396.284
• Mol file: 2098497-32-4.mol

Synonyms:

Chemical Property of (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Chemical Property:

• Boiling Point: 540.0±50.0 °C(Predicted)
• Density: 1.400±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(4aS,9bR)-Ethyl6-bromo-5-(2-(methylamino)-2-oxoethyl)-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

There total 8 articles about (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate 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:

chloroacetylmethylamide (96-30-0) + (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate (1059630-08-8) → (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (2098497-32-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; potassium iodide; In 1,4-dioxane; at 103 ℃; for 48h;

Reference yield:

[4aS,9bR]-6-bromo-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (1059630-07-7) → (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (2098497-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran

2: potassium iodide; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / Reflux

With triethylamine; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1358/dof.2015.040.10.2387229

Reference yield:

racemic cis 6-bromo-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole → (4aS,9bR)-ethyl 6-bromo-5-(2-(methylamino)-2-oxoethyl)-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (2098497-32-4)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / 40 - 50 °C / Inert atmosphere

2: sodium carbonate / tetrahydrofuran / 1.33 h / 25 °C / Inert atmosphere

3: potassium iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 20 - 102 °C

With sodium carbonate; N-ethyl-N,N-diisopropylamine; potassium iodide; In tetrahydrofuran; methanol; N,N-dimethyl acetamide;

upstream raw materials:

chloroacetylmethylamide

(4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate

2-bromophenylhydrazine hydrochloride

piperidine-4,4-diol hydrochloride

Downstream raw materials:

(6bR,10aS)-ethyl 2,3,6b,9,10,10a-hexahydro-3-methyl-2-oxo-1H-pyrido[3‘,4’:4,5]-pyrrolo[1,2,3-de]quinoxaline-8-carboxylate

(6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3‘,4’:4,5]-pyrrolo[1,2,3-de]quinoxaline-8-carboxylate

(6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido-[3’,4’:4,5]-pyrrolo[1,2,3-de]quinoxaline

Refernces

• 1、 Cole. "ITI-007". . p. 643 - 650. Retrieved 2015/11/24.