(1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole

Base Information

• Chemical Name: (1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole
• CAS No.: 1171123-83-3
• Molecular Formula: C₃₁H₃₆N₂O₃Si
• Molecular Weight: 512.724
• Mol file: 1171123-83-3.mol

Synonyms:(1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole

Chemical Property of (1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole

There total 1 articles about (1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole 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: 74.0%

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) + L-tryptophan methyl ester (4299-70-1) → (1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole (1171123-83-3) + (1R,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole (1309597-56-5)

Guidance literature:

3-(tert-butyldiphenylsilyloxy)-1-propanal; L-tryptophan methyl ester; In dichloromethane; at 0 ℃; for 40h; Inert atmosphere; Molecular sieve;

With trifluoroacetic acid; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201100147

Reference yield: 100.0%

(1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole (1171123-83-3) + but-2-yn-1-yl methanesulfonate (61493-85-4) → (1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole (1309597-50-9)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201100147

Reference yield:

(1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole (1171123-83-3) → C38H46N2O3Si

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / methanol / 0 - 20 °C / Inert atmosphere

2.1: dmap / acetonitrile / 2 h / 20 °C / Inert atmosphere

3.1: methanol; water; sodium hydroxide / tetrahydrofuran / 24 h / 20 °C

4.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran; acetonitrile / 0.25 h / 20 °C / Inert atmosphere

4.2: 0.08 h / 0 °C / Inert atmosphere

4.3: 2 h / Reflux; Inert atmosphere

With 4-methyl-morpholine; methanol; dmap; water; potassium carbonate; sodium hydroxide; isobutyl chloroformate; In tetrahydrofuran; methanol; acetonitrile; 4.1: Barton reaction / 4.2: Barton reaction / 4.3: Barton reaction;

DOI:10.1002/ejoc.201100147

upstream raw materials:

3-(tert-butyldiphenylsilyloxy)-1-propanal

L-tryptophan methyl ester

Downstream raw materials:

(1S,3S)-9-tert-butyl 3-methyl-2-(but-2-ynyl)-1-[2-(tert-butyldiphenylsilyloxy)ethyl]-3,4-dihydro-1H-pyrido[3,4-b]indole-3,9(2H)-dicarboxylate

(S)-9-(tert-butoxycarbonyl)-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole-3-carboxylic acid

methyl (E)-2-((2S,3S,12bS)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-methoxyacrylate

(1S,3S)-3-methyloxycarbonyl-2,3,4,9-tetrahydro-2-(2-butynyl)-1-(tert-butyldiphenylsilyloxyethyl)-1H-pyrido[3,4-b]indole