(2R)-2-(3,5-dimethylphenyl)pyrrolidine

Base Information

• Chemical Name: (2R)-2-(3,5-dimethylphenyl)pyrrolidine
• CAS No.: 1213509-59-1
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Mol file: 1213509-59-1.mol

Synonyms:(2R)-2-(3,5-dimethylphenyl)pyrrolidine

Chemical Property of (2R)-2-(3,5-dimethylphenyl)pyrrolidine

Chemical Property:

• PSA: 12.03000
• LogP: 3.05670

Purity/Quality:

99.00% ^*data from raw suppliers

(2R)-2-(3,5-DIMETHYLPHENYL)PYRROLIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R)-2-(3,5-dimethylphenyl)pyrrolidine

There total 3 articles about (2R)-2-(3,5-dimethylphenyl)pyrrolidine 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: 98.0%

C12H15N*H(1+) → (2R)-2-(3,5-dimethylphenyl)pyrrolidine (1213509-59-1)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-f-spiroPhos; hydrogen; In tetrahydrofuran; at 30 ℃; for 10h; under 7600.51 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/acs.orglett.7b01828

Reference yield: 93.0%

2-(3',5'-dimethylphenyl)-1-pyrroline (765312-46-7) → (2R)-2-(3,5-dimethylphenyl)pyrrolidine (1213509-59-1)

Guidance literature:

With diethoxymethylane; diethylzinc; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); In tetrahydrofuran; toluene; at 4 ℃; for 48h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/adsc.202001043

Reference yield:

5-bromo-1,3-xylene (556-96-7) → (2R)-2-(3,5-dimethylphenyl)pyrrolidine (1213509-59-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: magnesium; iodine / tetrahydrofuran / Reflux

1.2: 2 h / -78 °C / Inert atmosphere; Schlenk technique; Glovebox

2.1: trifluoroacetic acid / 1 h / Inert atmosphere; Schlenk technique; Glovebox

3.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-f-spiroPhos; hydrogen / tetrahydrofuran / 10 h / 30 °C / 7600.51 Torr / Autoclave

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (R,R)-f-spiroPhos; hydrogen; iodine; magnesium; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/acs.orglett.7b01828

upstream raw materials:

5-bromo-1,3-xylene

2-(3',5'-dimethylphenyl)-1-pyrroline

Downstream raw materials:

4-[4-[[(2R)-2-(3,5-dimethylphenyl)pyrrolidin-1-yl]methyl]phenoxy]-3-fluorobenzamide

Refernces

• 1、 Zhang, Ying,Yan, Qiaozhi,Zi, Guofu,Hou, Guohua. "Enantioselective Direct Synthesis of Free Cyclic Amines via Intramolecular Reductive Amination". . p. 4215 - 4218. Retrieved 2017/08/23.