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

Base Information

Chemical Name:(4S,4aR,7aR)-5,5-difluoro-4-(2-fluorophenyl)-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine
CAS No.:1526936-64-0
Molecular Formula:C₁₄H₁₅F₃N₂O
Molecular Weight:284.281
Hs Code.:

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

There total 7 articles about (4S,4aR,7aR)-5,5-difluoro-4-(2-fluorophenyl)-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: 80.0%

: cyanogen bromide

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

: 1526936-64-0
(4S,4aR,7aR)-5,5-difluoro-4-(2-fluorophenyl)-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

Guidance literature:: With ethanol; In acetonitrile; at 85 ℃; for 22h; Sealed tube;

Reference yield:

: 930-30-3
cyclopent-2-enone

: 1526936-64-0
(4S,4aR,7aR)-5,5-difluoro-4-(2-fluorophenyl)-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

: 1526936-64-0
(4S,4aR,7aR)-5,5-difluoro-4-(2-fluorophenyl)-4-methyl-4,4a,5,6,7,7a-hexahydrocyclopenta[e][1,3]oxazin-2-ylamine

Guidance literature:: Multi-step reaction with 5 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

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