(1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide

Base Information

Chemical Name:(1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide
CAS No.:693245-67-9
Molecular Formula:C₁₈H₂₂F₆N₂O
Molecular Weight:396.376
Hs Code.:

Synonyms:(1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide

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Chemical Property of (1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide

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Technology Process of (1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide

There total 7 articles about (1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide 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%

: tert-butyl (3-((3,5-bis(trifluoromethyl)benzyl)carbamoyl)-3-isopropylcyclopentyl)carbamate

: 693245-67-9
(1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/jm4011737

Reference yield:

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 693245-67-9
(1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 24 h

1.2: 72 h / 20 °C

2.1: dichloromethane / 24 h / 20 °C

3.1: n-butyllithium; lithium diisopropyl amide / tetrahydrofuran; hexane / 0.33 h

3.2: 6 h / 0 °C

4.1: hydrogenchloride / tetrahydrofuran / 3 h / 20 °C

4.2: 20 °C

5.1: methanol; lithium hydroxide; water / tetrahydrofuran / 18 h / 80 °C

6.1: 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C

7.1: hydrogenchloride / 1,4-dioxane / 1.5 h / 20 °C

With hydrogenchloride; methanol; lithium hydroxide; n-butyllithium; 1-hydroxy-7-aza-benzotriazole; water; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; ethyl acetate;

Reference yield:

: 624734-29-8
(1S,3R)-methyl-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylate

: 693245-67-9
(1S,3R)-3-amino-N-[3,5-bis(trifluoromethyl)benzyl]-1-isopropylcyclopentane-1-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1: lithium hydroxide / water / 4 h / Reflux

2: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; dmap / dichloromethane / 24 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With dmap; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; lithium hydroxide; In dichloromethane; water;
DOI:10.1021/jm4011737