[(4aS)-2,4a,9-trimethyl-4,9a-dihydro-3H-oxazino[6,5-b]indol-6-yl] N-methylcarbamate

Base Information

• Chemical Name: [(4aS)-2,4a,9-trimethyl-4,9a-dihydro-3H-oxazino[6,5-b]indol-6-yl] N-methylcarbamate
• CAS No.: 25573-43-7
• Molecular Formula: C₁₅H₂₁N₃O₃
• Molecular Weight: 291.35
• DSSTox Substance ID: DTXSID30877868
• Mol file: 25573-43-7.mol

Synonyms:SCHEMBL679454;DTXSID30877868;NS00086502

Chemical Property of [(4aS)-2,4a,9-trimethyl-4,9a-dihydro-3H-oxazino[6,5-b]indol-6-yl] N-methylcarbamate

Chemical Property:

• Melting Point: 129°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 54.04000
• Density: 1.189g/cm³
• LogP: 2.09930
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 291.15829154
• Heavy Atom Count: 21
• Complexity: 419

Purity/Quality:

99% ^*data from raw suppliers

ESERIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCN(OC1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
• Isomeric SMILES: C[C@@]12CCN(OC1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
• Uses: (4aS,9aS)-2,4a,9-Trimethyl-2,3,4,4a,9,9a-hexahydro-[1,2]oxazino[6,5-b]indol-6-yl methylcarbamate is an important chemical reagent used in biological study and has therapeutic use.

Technology Process of [(4aS)-2,4a,9-trimethyl-4,9a-dihydro-3H-oxazino[6,5-b]indol-6-yl] N-methylcarbamate

There total 16 articles about [(4aS)-2,4a,9-trimethyl-4,9a-dihydro-3H-oxazino[6,5-b]indol-6-yl] N-methylcarbamate 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: 75.0%

3-<2-(N-hydroxy-N-methylamino)ethyl>-1,3-dimethyl-5-(N-methylcarbamoyloxy)indol-2-(3H)-one (105780-81-2) → (+/-)-geneserine (25573-43-7,34021-37-9,105816-13-5)

Guidance literature:

With di(tert-butyl)aluminium hydride; In 1,2-dimethoxyethane; hexane; at -75 ℃; for 0.5h;

Reference yield:

3-allyl-1,3-dimethyl-5-methoxy-2-oxo-1,3-dihydroindole (105780-78-7) → (+/-)-geneserine (25573-43-7,34021-37-9,105816-13-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / BBr₃ / CH₂Cl₂

2: 91 percent / NaH / tetrahydrofuran

3: OsO₄, NaIO₄ / diethyl ether; H₂O

4: 1.) KOH, 2.) NaCNBH₃ / 1.) MeOH

5: 75 percent / i-Bu₂AlH / 1,2-dimethoxy-ethane / 0.5 h / -75 °C

With potassium hydroxide; sodium periodate; osmium(VIII) oxide; boron tribromide; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water;

DOI:10.1039/c39860000904

Reference yield:

3-allyl-5-hydroxy-1,3-dimethylindol-2(3H)-one (105780-79-8) → (+/-)-geneserine (25573-43-7,34021-37-9,105816-13-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / NaH / tetrahydrofuran

2: OsO₄, NaIO₄ / diethyl ether; H₂O

3: 1.) KOH, 2.) NaCNBH₃ / 1.) MeOH

4: 75 percent / i-Bu₂AlH / 1,2-dimethoxy-ethane / 0.5 h / -75 °C

With potassium hydroxide; sodium periodate; osmium(VIII) oxide; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; water;

DOI:10.1039/c39860000904

upstream raw materials:

3-<2-(N-hydroxy-N-methylamino)ethyl>-1,3-dimethyl-5-(N-methylcarbamoyloxy)indol-2-(3H)-one

3-allyl-1,3-dimethyl-5-methoxy-2-oxo-1,3-dihydroindole

3-allyl-5-hydroxy-1,3-dimethylindol-2(3H)-one

methyl (2-(1-(hydroxymethyl)-1-methyl-3-butenyl)-4-methoxyphenyl)carbamate