methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate

Base Information

• Chemical Name: methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate
• CAS No.: 1403934-21-3
• Molecular Formula: C₂₉H₄₂ClNO₃
• Molecular Weight: 488.11
• Mol file: 1403934-21-3.mol

Synonyms:methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate

Chemical Property of methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate

There total 8 articles about methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate 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: 71.0%

methanol (67-56-1) + tert-butyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate (1403934-19-9) → methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate (1403934-21-3)

Guidance literature:

With thionyl chloride; for 4h; Reflux;

DOI:10.1021/jo301830j

Reference yield:

hexanal (66-25-1) → methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate (1403934-21-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: (-)-diisopinocamphenylborane chloride / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C

2.2: 18 h / 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane; ethanol / 24 h / 40 °C

4.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

5.1: thionyl chloride / 4 h / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; thionyl chloride; sodium hydride; (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; mineral oil;

DOI:10.1021/jo301830j

Reference yield:

(R)-4-(benzyloxy)non-1-ene (397251-81-9) → methyl (R,R,R)-3-[N-(3′-chloropropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate (1403934-21-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane; ethanol / 24 h / 40 °C

2.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

3.1: thionyl chloride / 4 h / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; thionyl chloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo301830j

upstream raw materials:

tert-butyl (RS,E) 5-(benzyloxy)dec-2-enoate

(R)-4-(benzyloxy)non-1-ene

tert-butyl (R,E) 5-(benzyloxy)dec-2-enoate

hexanal

Downstream raw materials:

methyl (R,R,R)-3-[N-(3'-azidopropyl)-N-(α-methylbenzyl)amino]-5-(benzyloxy)decanoate