(3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate
• CAS No.: 1329998-87-9
• Molecular Formula: C₃₆H₅₁ClF₂N₄O₇
• Molecular Weight: 725.273
• Mol file: 1329998-87-9.mol

Synonyms:(3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate

Chemical Property of (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate

There total 12 articles about (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-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: 90.0%

2-(3-chlorophenyl)-2,2-difluoroethylamine hydrochloride (780769-49-5) + (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-oxoethoxy)pyrrolidine-1-carboxylate (1237495-45-2) → (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate (1329998-87-9)

Guidance literature:

With sodium tris(acetoxy)borohydride; triethylamine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jm200411j

Reference yield: 90.0%

→ (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate (1329998-87-9)

Guidance literature:

Reference yield:

tert-butyl (4,6-dimethylpyridin-2-yl)carbamate (848472-36-6) → (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((2,2-difluoro-2-(3-chlorophenyl)ethyl)amino)ethoxy)pyrrolidine-1-carboxylate (1329998-87-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-butyllithium / -78 - 20 °C

1.2: -78 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 30 h

3.1: dmap / tetrahydrofuran / 24 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

6.1: sodium carbonate / methanol; water / 0.5 h / 35 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 5 h / 45 °C

8.1: ozone / dichloromethane / 0.67 h / -78 °C

9.1: dimethylsulfide / dichloromethane / -78 - 20 °C

10.1: sodium tris(acetoxy)borohydride; triethylamine / dichloromethane / 3 h / 20 °C

With 1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; dimethylsulfide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; sodium carbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Mitsunobu reaction;

DOI:10.1021/jm200411j

upstream raw materials:

tert-butyl (4,6-dimethylpyridin-2-yl)carbamate

(3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate

2-(3-chlorophenyl)-2,2-difluoroethylamine hydrochloride

(3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-oxoethoxy)pyrrolidine-1-carboxylate