tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate

Base Information

• Chemical Name: tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate
• CAS No.: 1380521-86-7
• Molecular Formula: C₃₀H₃₄F₃NO₃
• Molecular Weight: 513.6
• Mol file: 1380521-86-7.mol

Synonyms:tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate

Chemical Property of tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate

There total 2 articles about tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate 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: 86.0%

tert-butyl (E)-4-(2',4',5'-trifluorophenyl)but-2-enoate (1380521-84-5) + (R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine (14429-03-9,120343-46-6,140408-66-8) → tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate (1380521-86-7)

Guidance literature:

(R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

tert-butyl (E)-4-(2',4',5'-trifluorophenyl)but-2-enoate; In tetrahydrofuran; at -78 ℃; for 2h; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tetlet.2012.04.025

Reference yield:

tert-butyl diethylphosphonoacetate (27784-76-5) → tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate (1380521-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: methylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.25 h

1.2: 15 h / Reflux

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C

2.2: 2 h / -78 °C

With n-butyllithium; methylmagnesium bromide; In tetrahydrofuran; diethyl ether; 1.2: Wadsworth-Emmons reaction;

DOI:10.1016/j.tetlet.2012.04.025

Reference yield:

tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-4-(2',4',5'-trifluorophenyl)butanoate (1380521-86-7) → sitagliptin (486460-32-6,823817-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / water / 6 h / Reflux

2: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / chloroform / 16 h / 20 °C

3: 20 wt.% Pd(OH)2 on activated carbon; hydrogen / methanol / 24 h / 3800.26 Torr

With hydrogenchloride; 20 wt.% Pd(OH)2 on activated carbon; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In methanol; chloroform; water;

DOI:10.1016/j.tetlet.2012.04.025

upstream raw materials:

tert-butyl (E)-4-(2',4',5'-trifluorophenyl)but-2-enoate

(R)-N-benzyl-N-(α-methyl-p-methoxybenzyl)amine

tert-butyl diethylphosphonoacetate

Downstream raw materials:

sitagliptin phosphate

(R)-N-benzyl-1-(2',4',5'-trifluorophenyl)-4-oxo-4-{3''-(trifluoromethyl)-5'',6''-dihydro-1'',2'',4''-triazolo[4,3-α]pyrazin-7''(8''H)-yl}butan-2-amine

sitagliptin