ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate

Base Information

• Chemical Name: ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate
• CAS No.: 1204820-82-5
• Molecular Formula: C₃₂H₃₆F₇N₃O₃
• Molecular Weight: 643.645

Synonyms:ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate

Chemical Property of ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate

Chemical Property:

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Technology Process of ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate

There total 2 articles about ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate 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: 14.54%

2-(R)-(4-fluoro-2-methyl-phenyl)-4-oxo-piperidine-1-carboxylic acid [1-(S)-(3,5-bis-trifluoromethyl-phenyl)ethyl]-methylamide (414910-07-9) + ethyl (1R,5R)-3-azabicyclo[3.1.0]hexane-1-carboxylate trifluoroacetate (1204820-74-5) → ethyl (1R,5R)-3-[(2R,4R)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (1204820-81-4) + ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (1204820-82-5)

Guidance literature:

ethyl (1R,5R)-3-azabicyclo[3.1.0]hexane-1-carboxylate trifluoroacetate; With triethylamine; In methanol; at 25 ℃; for 0.5h; Inert atmosphere;

2-(R)-(4-fluoro-2-methyl-phenyl)-4-oxo-piperidine-1-carboxylic acid [1-(S)-(3,5-bis-trifluoromethyl-phenyl)ethyl]-methylamide; In methanol; at 25 ℃;

With methanol; sodium cyanoborohydride; at 25 ℃;

Reference yield: 14.5%

2-(R)-(4-fluoro-2-methyl-phenyl)-4-oxo-piperidine-1-carboxylic acid [1-(S)-(3,5-bis-trifluoromethyl-phenyl)ethyl]-methylamide (414910-07-9) + (R)-3-azabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester (63618-09-7) → ethyl 3-[(2R,4R)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (1204820-79-0) + ethyl (1S,5S)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (1204820-83-6) + ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (1204820-82-5)

Guidance literature:

2-(R)-(4-fluoro-2-methyl-phenyl)-4-oxo-piperidine-1-carboxylic acid [1-(S)-(3,5-bis-trifluoromethyl-phenyl)ethyl]-methylamide; (R)-3-azabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester; In methanol; at 20 ℃; for 0.166667h;

With methanol; sodium cyanoborohydride; at 20 ℃; for 3h;

In hexane; isopropyl alcohol; Resolution of diastereomers;

Reference yield: 98.0%

ethyl (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (1204820-82-5) → sodium (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate (1204820-88-1)

Guidance literature:

With water; sodium hydroxide; In methanol; at 90 ℃; for 1h; Product distribution / selectivity; Microwave irradiation;

upstream raw materials:

2-(R)-(4-fluoro-2-methyl-phenyl)-4-oxo-piperidine-1-carboxylic acid [1-(S)-(3,5-bis-trifluoromethyl-phenyl)ethyl]-methylamide

(R)-3-azabicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester

ethyl (1R,5R)-3-azabicyclo[3.1.0]hexane-1-carboxylate trifluoroacetate

Downstream raw materials:

sodium (1R,5R)-3-[(2R,4S)-1-{[{(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl}(methyl)amino]carbonyl}-2-(4-fluoro-2-methylphenyl)-4-piperidinyl]-3-azabicyclo[3.1.0]hexane-1-carboxylate

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