methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

Base Information

• Chemical Name: methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate
• CAS No.: 2671-54-7
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.433
• Mol file: 2671-54-7.mol

Synonyms:methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

Chemical Property of methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

There total 5 articles about methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-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:

(4aS,13bS,14aS)-1-(1,3-dithian-2-ylidene)-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinolin-2(1H)-one → 16-Methoxycarbonyl-alloyohimbanon-(17) (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) + methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate (2671-54-7)

Guidance literature:

(4aS,13bS,14aS)-1-(1,3-dithian-2-ylidene)-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinolin-2(1H)-one; With toluene-4-sulfonic acid; In methanol; dichloromethane; for 0.166667h;

With boron trifluoride diethyl etherate; mercury dichloride; In methanol; dichloromethane; at 40 ℃; for 24h; Overall yield = 62 percent; Overall yield = 54 mg;

DOI:10.1021/jacs.9b12319

Reference yield:

ethyl (3S,4S)-3-(2-ethoxy-2-oxoethyl)-2-oxo-3,4-dihydro-2H-pyran-4-carboxylate → 16-Methoxycarbonyl-alloyohimbanon-(17) (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) + methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate (2671-54-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium carbonate / dichloromethane; water / 16 h / 20 °C

1.2: 48 h / 40 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 8 h / 0 °C

2.2: 16 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / toluene; hexane / 0.5 h / 0 °C

3.2: 0 °C

3.3: 16 h / 0 - 20 °C

4.1: toluene-4-sulfonic acid / dichloromethane; methanol / -78 - 45 °C

5.1: toluene-4-sulfonic acid / dichloromethane; methanol / 0.17 h

5.2: 24 h / 40 °C

With n-butyllithium; dimethylsulfide borane complex; sodium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;

DOI:10.1021/jacs.9b12319

Reference yield:

ethyl (2S,3S,12bS)-3-(2-ethoxy-2-oxoethyl)-4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-2-carboxylate → 16-Methoxycarbonyl-alloyohimbanon-(17) (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) + methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate (2671-54-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 8 h / 0 °C

1.2: 16 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / toluene; hexane / 0.5 h / 0 °C

2.2: 0 °C

2.3: 16 h / 0 - 20 °C

3.1: toluene-4-sulfonic acid / dichloromethane; methanol / -78 - 45 °C

4.1: toluene-4-sulfonic acid / dichloromethane; methanol / 0.17 h

4.2: 24 h / 40 °C

With n-butyllithium; dimethylsulfide borane complex; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/jacs.9b12319

Downstream raw materials:

rauwolscine