(S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one

Base Information

• Chemical Name: (S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one
• CAS No.: 1621326-32-6
• Molecular Formula: C₁₈H₁₅N₃O₄
• Molecular Weight: 337.335
• Mol file: 1621326-32-6.mol

Synonyms:(S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one

Chemical Property of (S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

(S)-4'-nitro-Blebbistatin ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one

There total 8 articles about (S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one 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:

C19H19N3O4 → (R)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one + (S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one (1621326-32-6) + C38H36N6O8

Guidance literature:

C₁₉H₁₉N₃O₄; With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;

With (1R)-(-)-(8,8-dichloro-10-camphorsulfonyl) oxaziridine; In tetrahydrofuran; at -15 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.ejmech.2017.04.072

Reference yield:

1-(4-nitrophenyl)-6-methyl-1H,2H,3H,4H,9H-pyrrolo[2,3-b]quinolin-4-one (1621326-30-4) → (R)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one + (S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one (1621326-32-6)

Guidance literature:

1-(4-nitrophenyl)-6-methyl-1H,2H,3H,4H,9H-pyrrolo[2,3-b]quinolin-4-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine; In tetrahydrofuran; at -78 - -10 ℃; for 16h; Overall yield = 54 %; Further stages; Inert atmosphere;

DOI:10.1002/anie.201403540

Reference yield:

2-carbomethoxyaniline (134-20-3) → (R)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one + (S)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one (1621326-32-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / 48 h / 60 °C

2.1: trichlorophosphate / dichloromethane / 3 h

2.2: 18 h / 50 °C / Inert atmosphere; Reflux

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 16 h / -78 - -10 °C / Inert atmosphere

With sulfuric acid; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; dichloromethane; 4.2: |Davis' Oxaziridine Oxidations;

DOI:10.1002/anie.201403540

upstream raw materials:

2-carbomethoxyaniline

1-(4-nitrophenyl)pyrrolidin-2-one

2-amino-5-methylbenzoic acid methyl ester

1-(4-nitrophenyl)-6-methyl-1H,2H,3H,4H,9H-pyrrolo[2,3-b]quinolin-4-one