tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate

Base Information

• Chemical Name: tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate
• CAS No.: 1227062-94-3
• Molecular Formula: C₂₇H₃₈INO₃
• Molecular Weight: 551.508
• Mol file: 1227062-94-3.mol

Synonyms:tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate

Chemical Property of tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate

There total 7 articles about tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate 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: 91.0%

tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-hydroxyheptanoate (1227062-93-2) → tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate (1227062-94-3)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; acetonitrile; at 65 ℃; for 2h;

DOI:10.1055/S-0029-1219346

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate (1227062-94-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

1.2: 16 h / -78 - 20 °C / Inert atmosphere

1.3: 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

3.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 16 h / 65 °C

With 1H-imidazole; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; hexane; toluene; acetonitrile;

DOI:10.1016/j.tet.2011.09.038

Reference yield:

1(R)-(4-methoxyphenyl)-ethylamine (6298-96-0,22038-86-4,35600-82-9,41851-59-6) → tert-butyl (3R,αR)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-iodoheptanoate (1227062-94-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

3.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 16 h / 65 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; iodine; triphenylphosphine; In tetrahydrofuran; hexane; toluene; acetonitrile;

DOI:10.1016/j.tet.2011.09.038

upstream raw materials:

tert-butyl (R,R)-3-[N-benzyl-N-(α-methyl-p-methoxybenzyl)amino]-7-hydroxyheptanoate

3,4,5,6-tetrahydro-2H-pyran-2-one

tert-butyl diethylphosphonoacetate

1(R)-(4-methoxyphenyl)-ethylamine

Downstream raw materials:

tert-butyl (R)-2-[N⁽¹⁾-benzylpiperidin-2-yl]acetate

4-Methoxystyrene

(R)-2-[N⁽¹⁾-benzylpiperidin-2-yl]ethanal

(R)-N⁽¹⁾-benzyl-2-allylpiperidine

Refernces

• 1、 Davies, Stephen G.,Fletcher, Ai M.,Hughes, Deri G.,Lee, James A.,Price, Paul D.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Thomson, James E.,Williams, Oliver M.H.. "Asymmetric synthesis of piperidines and octahydroindolizines using a one-pot ring-closure/N-debenzylation procedure". experimental part. p. 9975 - 9992. Retrieved 2012/02/15.