tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate

Base Information

• Chemical Name: tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate
• CAS No.: 882856-76-0
• Molecular Formula: C₂₃H₂₇F₃N₂O₂
• Molecular Weight: 420.475
• Mol file: 882856-76-0.mol

Synonyms:tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate

Chemical Property of tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate

There total 17 articles about tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate 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:

methyl tert butyl [trans-1-benzyl-6-oxo-4-(2,4,5-trifluorophenyl)piperidin-3-yl]carbamate → tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate (882856-76-0) + tert-butyl [(3S,4S)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-yl]carbamate

Guidance literature:

methyl tert butyl [trans-1-benzyl-6-oxo-4-(2,4,5-trifluorophenyl)piperidin-3-yl]carbamate; With borane; In tetrahydrofuran; for 3h; Heating / reflux;

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 2h; Heating / reflux;

With di-tert-butyl dicarbonate; sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 10h;

Reference yield:

C20H18F3NO3 → tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate (882856-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aq. LiOH / tetrahydrofuran; methanol / 60 °C

2.1: diphenyl phosphoryl azide; triethylamine / toluene / Heating

3.1: Heating

4.1: H₂ / Pd(OH)2 / methanol / 2327.23 Torr

5.1: BH₃ / tetrahydrofuran / Heating

5.2: HCl / tetrahydrofuran / Heating

6.1: tetrahydrofuran; ethyl acetate / Heating

With lithium hydroxide; diphenyl phosphoryl azide; borane; hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethyl acetate; toluene; 2.1: Curtius rearrangement;

DOI:10.1016/j.bmcl.2007.05.087

Reference yield:

C19H16F3NO3 → tert-butyl (3R,4R)-1-benzyl-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate (882856-76-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diphenyl phosphoryl azide; triethylamine / toluene / Heating

2.1: Heating

3.1: H₂ / Pd(OH)2 / methanol / 2327.23 Torr

4.1: BH₃ / tetrahydrofuran / Heating

4.2: HCl / tetrahydrofuran / Heating

5.1: tetrahydrofuran; ethyl acetate / Heating

With diphenyl phosphoryl azide; borane; hydrogen; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethyl acetate; toluene; 1.1: Curtius rearrangement;

DOI:10.1016/j.bmcl.2007.05.087

upstream raw materials:

di-tert-butyl dicarbonate

ethyl 3-(2,4,5-trifluorophenyl)acrylate

dimethyl 2-cyano-3-(2,4,5-trifluorophenyl)pentanedioate

benzyl bromide

Downstream raw materials:

tert-butyl(3R,4R)-4-(2,4,5-trifluorophenyl)piperidin-3-ylcarbamate

C₂₄H₃₂F₃N₅O₂

C₂₄H₂₈F₅N₅O₂

C₂₄H₃₀F₃N₅O₃

Refernces

• 1、 Cox, Jason M.,Harper, Bart,Mastracchio, Anthony,Leiting, Barbara,Sinha Roy, Ranabir,Patel, Reshma A.,Wu, Joseph K.,Lyons, Kathryn A.,He, Huaibing,Xu, Shiyao,Zhu, Bing,Thornberry, Nancy A.,Weber, Ann E.,Edmondson, Scott D.. "Discovery of 3-aminopiperidines as potent, selective, and orally bioavailable dipeptidyl peptidase IV inhibitors". . p. 4579 - 4583. Retrieved 2008/02/11.