tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate

Base Information

• Chemical Name: tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate
• CAS No.: 1352429-45-8
• Molecular Formula: C₁₈H₂₇NO₂
• Molecular Weight: 289.418
• Mol file: 1352429-45-8.mol

Synonyms:tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate

Chemical Property of tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate

There total 8 articles about tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate 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 (2′S,αR)-2-[N(1′)-(α-methylbenzyl)-2′,5′-dihydro-1H-pyrrol-2′-yl]acetate → tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate (1352429-45-8)

Guidance literature:

With Wilkinson's catalyst; hydrogen; In ethyl acetate; at 20 ℃; for 16h; under 1520.1 Torr;

DOI:10.1021/acs.joc.7b00837

Reference yield:

tert-butyl (E,R)-6-[N-(α-methylbenzyl)amino]hex-2-enoate (1352429-42-5) → tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate (1352429-45-8) + tert-butyl (2S,αR)-2-[N(1)-(α-methylbenzyl)pyrrolidin-2-yl]acetate

Guidance literature:

tert-butyl (E,R)-6-[N-(α-methylbenzyl)amino]hex-2-enoate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; hexane; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tet.2011.09.038

Reference yield:

tert-butyl (E,R)-6-[N-benzyl-N-(α-methylbenzyl)amino]hex-2-enoate (1352429-34-5) → tert-butyl (R,R)-2-[N(1′)-(α-methylbenzyl)pyrrolidin-2′-yl]acetate (1352429-45-8) + tert-butyl (2S,αR)-2-[N(1)-(α-methylbenzyl)pyrrolidin-2-yl]acetate

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium cerium (IV) nitrate; water / acetonitrile / 16 h / 20 °C

2: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

With n-butyllithium; ammonium cerium (IV) nitrate; water; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1016/j.tet.2011.09.038

upstream raw materials:

(E)-6-oxo-hex-2-enoic acid tert-butyl ester

tert-butyl (E,R)-6-[N-benzyl-N-(α-methylbenzyl)amino]hex-2-enoate

tert-butyl (E,R)-6-[N-(α-methylbenzyl)amino]hex-2-enoate

tert-butyl diethylphosphonoacetate