(R)-tert-butyl 2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-ylcarbamate

Base Information

• Chemical Name: (R)-tert-butyl 2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-ylcarbamate
• CAS No.: 957121-34-5
• Molecular Formula: C26H35N3O4Si
• Molecular Weight: 481.66
• Mol file: 957121-34-5.mol

Synonyms:tert-Butyl 8-quinolyl carbonate;O-tert-butoxycarbonyl-8-hydroxyquinoline;tert-butyl (quinolin-8-yl)carbonate;tert-butyl (R)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate;8-t-Butoxycarbonyloxychinolin;tert-Butyl-chinolyl-(8)-carbonat;carbonic acid tert-butyl ester quinolin-8-yl ester;tert-Butyl-<8>chinolyl-carbonat;

Chemical Property of (R)-tert-butyl 2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-ylcarbamate

Chemical Property:

• PSA: 80.76000
• LogP: 5.26210

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl 2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-ylcarbamate

There total 13 articles about (R)-tert-butyl 2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-ylcarbamate 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:

tert-butyl (+/-)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate (1033608-31-9) → tert-butyl (S)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate (957121-35-6) + tert-butyl (R)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate (957121-34-5)

Guidance literature:

With CHIRALPAK AD; In ethanol; Resolution of racemate;

Reference yield:

5-amino-1‘-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3’-pyrrolo[2,3-b]pyridin]-2’(1’H)-one (879132-50-0,879132-51-1,939384-55-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (S)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate (957121-35-6) + tert-butyl (R)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate (957121-34-5)

Guidance literature:

In chloroform; for 17h; Heating / reflux;

Reference yield:

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (879132-46-4) → tert-butyl (R)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate (957121-34-5)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridinium hydrobromide perbromide / 1,4-dioxane / 1.5 h / 20 °C

2: ammonium chloride; zinc / tetrahydrofuran; water / 3 h

3: caesium carbonate / N,N-dimethyl-formamide / 18.08 h

4: hydrogen / palladium 10% on activated carbon / ethanol / 18 h / 760.05 Torr

5: chloroform / 17 h / Heating / reflux

6: Resolution of racemate

With hydrogen; pyridinium hydrobromide perbromide; ammonium chloride; caesium carbonate; zinc; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; ethanol; chloroform; water; N,N-dimethyl-formamide;

upstream raw materials:

5-amino-1‘-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3’-pyrrolo[2,3-b]pyridin]-2’(1’H)-one

di-tert-butyl dicarbonate

tert-butyl (+/-)-(2'-oxo-1'-{[2-(trimethylsilyl)ethoxy]methyl}-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl)carbamate

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Downstream raw materials:

(R)-5-amino-1,3-dihydrospiro[indene-2,3’-pyrrolo[2,3-b]pyridin]-2’(1’H)-one

2-[5-(3,5-difluorophenyl)-3-ethyl-5-methyl-2,4-dioxoimidazolidin-1-yl]-N-[(2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl]acetamide

(2R)-5-{(1E)-3-[(7R,9aR)-7-(3,5-difluorophenyl)-9-oxohexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]prop-1-en-1-yl}-1,3-dihydrospiro[indene-2,3 '-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 5

(2R)-5-{(1E)-3-[2-(3,5-difluorophenyl)-5-(fluoromethyl)-2,4,5-trimethyl-6-oxopiperazin-1-yl]prop-1-en-1-yl}-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one