(4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

Base Information

Chemical Name:(4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine
CAS No.:1526936-76-4
Molecular Formula:C₁₄H₁₆F₃N₃O
Molecular Weight:299.296
Hs Code.:

Synonyms:(4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

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Chemical Property of (4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

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Technology Process of (4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

There total 8 articles about (4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine 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:

: 930-30-3
cyclopent-2-enone

: 1526936-76-4
(4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine; phenyl isocyanate / diethyl ether / 25 °C / Inert atmosphere

2.1: morpholinosulfur trifluoride / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.17 h / 70 - 78 °C / Inert atmosphere

3.2: 2.17 h / 70 - 78 °C

4.1: n-heptane; ethanol / Resolution of racemate

5.1: palladium 10% on activated carbon; ammonium formate / ethanol / 2.5 h / 22 °C

6.1: ethanol / acetonitrile / 22 h / 85 °C / Sealed tube

7.1: sulfuric acid; nitric acid / 2 h / 0 - 22 °C

8.1: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol / 1.5 h / 22 °C / 760.05 Torr

With n-butyllithium; ethanol; sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; ammonium formate; phenyl isocyanate; triethylamine; morpholinosulfur trifluoride; In tetrahydrofuran; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; toluene; acetonitrile;

Reference yield:

: 1526936-57-1
(1R,2R)-2-[(S)-1-amino-1-(2-fluorophenyl)ethyl]-3,3-difluorocyclopentanol

: 1526936-76-4
(4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

Guidance literature:: Multi-step reaction with 3 steps

1: ethanol / acetonitrile / 22 h / 85 °C / Sealed tube

2: sulfuric acid; nitric acid / 2 h / 0 - 22 °C

3: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol / 1.5 h / 22 °C / 760.05 Torr

With ethanol; sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; triethylamine; In ethanol; acetonitrile;

Reference yield:

: 59919-43-6,119458-73-0
rac-(3aR,6aR)-3-methyl-3a,5,6,6a-tetrahydrocyclopenta[d]isoxazol-4-one

: 1526936-76-4
(4S,4aR,7aR)-4-(5-amino-2-fluorophenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

Guidance literature:: Multi-step reaction with 7 steps

1.1: morpholinosulfur trifluoride / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.17 h / 70 - 78 °C / Inert atmosphere

2.2: 2.17 h / 70 - 78 °C

3.1: n-heptane; ethanol / Resolution of racemate

4.1: palladium 10% on activated carbon; ammonium formate / ethanol / 2.5 h / 22 °C

5.1: ethanol / acetonitrile / 22 h / 85 °C / Sealed tube

6.1: sulfuric acid; nitric acid / 2 h / 0 - 22 °C

7.1: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol / 1.5 h / 22 °C / 760.05 Torr

With n-butyllithium; ethanol; sulfuric acid; palladium 10% on activated carbon; hydrogen; nitric acid; ammonium formate; triethylamine; morpholinosulfur trifluoride; In tetrahydrofuran; ethanol; hexane; n-heptane; dichloromethane; toluene; acetonitrile;