tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate

Base Information

• Chemical Name: tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate
• CAS No.: 1252761-96-8
• Molecular Formula: C₂₁H₂₉BClNO₅
• Molecular Weight: 421.729
• Mol file: 1252761-96-8.mol

Synonyms:tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate

Chemical Property of tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate

There total 7 articles about tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate 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: 78.0%

tert-butyl (R)-4-(4-chloro-3-iodophenyl)-2-oxopyrrolidine-1-carboxylate (1252761-94-6) + bis(pinacol)diborane (73183-34-3) → tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate (1252761-96-8)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 85 ℃; Inert atmosphere;

Reference yield: 43.0%

(R)-4-(4-chloro-3-iodophenyl)pyrrolidin-2-one (1252761-95-7) + bis(pinacol)diborane (73183-34-3) → tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate (1252761-96-8)

Guidance literature:

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2011.08.006

Reference yield:

(R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-one (1252761-51-5) → tert-butyl (4R)-4-[4-chloro-3-(4,4,5,5-tetramethyl(1,3,2-dioxaborolan-2-yl))phenyl]-2-oxopyrrolidinecarboxylate (1252761-96-8)

Guidance literature:

Multi-step reaction with 3 steps

1: iron; acetic acid / 50 °C

2: hydrogenchloride; potassium iodide; sodium nitrite / water / 0 °C

3: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane; dichloromethane

With hydrogenchloride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; iron; acetic acid; potassium iodide; sodium nitrite; In 1,4-dioxane; dichloromethane; water; 2: Sandmeyer reaction;

DOI:10.1016/j.bmcl.2011.08.006

upstream raw materials:

tert-butyl (R)-4-(4-chloro-3-iodophenyl)-2-oxopyrrolidine-1-carboxylate

bis(pinacol)diborane

(R)-4-(3-amino-4-chlorophenyl)pyrrolidin-2-one

(R)-4-(4-chloro-3-nitrophenyl)pyrrolidin-2-one

Downstream raw materials:

C₂₃H₂₄ClNO₅

tert-butyl (R)-4-(4-chloro-3-hydroxyphenyl)-2-oxopyrrolidine-1-carboxylate

(3R)-4-amino-3-[4-chloro-3-(2-(4-pyridyl)ethoxy)phenyl]butanoic acid

C₁₇H₁₉ClN₂O₃