(4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate

Base Information

• Chemical Name: (4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate
• CAS No.: 1438392-93-8
• Molecular Formula: C₂₇H₂₆N₂O₃
• Molecular Weight: 426.515
• Mol file: 1438392-93-8.mol

Synonyms:(4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate

Chemical Property of (4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate

There total 5 articles about (4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate 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: 85.0%

1-(2,5-dimethylbenzyl)-1H-indol-3-yl acetate (1438392-80-3) + 2-chloro-1-phenyl-ethanone oxime (21572-32-7) → (4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate (1438392-93-8)

Guidance literature:

With silver (II) carbonate; 2CF₃O₃S^(1-)*Cu⁽²⁺⁾*0.5C₇H₈; (S)-2,2'-bis-1,1'-binaphthyl; In dichloromethane; at -78 - 23 ℃; for 48h; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/chem.201203435

Reference yield:

1-(2,5-dimethylbenzyl)-1H-indole (1177106-77-2) → (4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate (1438392-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; potassium hydroxide / acetonitrile / 12 h / 70 °C / Inert atmosphere

2: 2CF3O3S(1-)*Cu(2+)*0.5C7H8; (S)-2,2'-bis-1,1'-binaphthyl; silver (II) carbonate / dichloromethane / 48 h / -78 - 23 °C / Inert atmosphere; Molecular sieve

With silver (II) carbonate; 2CF₃O₃S^(1-)*Cu⁽²⁺⁾*0.5C₇H₈; palladium diacetate; (S)-2,2'-bis-1,1'-binaphthyl; potassium hydroxide; In dichloromethane; acetonitrile;

DOI:10.1002/chem.201203435

Reference yield:

indole (120-72-9) → (4aS,9aR)-9-(2,5-dimethylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indol-4a-yl acetate (1438392-93-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 23 °C / Inert atmosphere

1.2: 12 h / 0 - 23 °C / Inert atmosphere

2.1: palladium diacetate; potassium hydroxide / acetonitrile / 12 h / 70 °C / Inert atmosphere

3.1: 2CF3O3S(1-)*Cu(2+)*0.5C7H8; (S)-2,2'-bis-1,1'-binaphthyl; silver (II) carbonate / dichloromethane / 48 h / -78 - 23 °C / Inert atmosphere; Molecular sieve

With silver (II) carbonate; 2CF₃O₃S^(1-)*Cu⁽²⁺⁾*0.5C₇H₈; palladium diacetate; sodium hydride; (S)-2,2'-bis-1,1'-binaphthyl; potassium hydroxide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/chem.201203435

upstream raw materials:

indole

2,5-dimethylbenzyl chloride

1-(2,5-dimethylbenzyl)-1H-indole

1-(2,5-dimethylbenzyl)-1H-indol-3-yl acetate