(1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid

Base Information

• Chemical Name: (1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid
• CAS No.: 1379691-07-2
• Molecular Formula: C₂₂H₂₇NO₂
• Molecular Weight: 337.462
• Mol file: 1379691-07-2.mol

Synonyms:(1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid

Chemical Property of (1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid

There total 4 articles about (1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid 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: 44.0%

(1R,2S)-ethyl 2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylate (1379691-05-0) → (1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid (1379691-07-2)

Guidance literature:

(1R,2S)-ethyl 2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylate; With potassium tert-butylate; sodium hydride; In tert-butyl alcohol; Reflux;

With water; ammonium chloride; In tert-butyl alcohol;

DOI:10.1002/chem.201102847

Reference yield:

ethyl 2-(4-methylbenzenesulfonyloxy)cyclohexanecarboxylate (1315564-11-4) → (1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid (1379691-07-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C

2.2: -78 °C

3.1: potassium tert-butylate; sodium hydride / tert-butyl alcohol / Reflux

With n-butyllithium; potassium tert-butylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1002/chem.201102847

Reference yield:

(1R,2S)-ethyl 2-hydroxycyclohexanecarboxylate (1655-06-7,6125-55-9,6149-52-6,29569-79-7,61586-78-5,77026-73-4,119068-36-9,119068-37-0,3444-72-2) → (1S,2S)-2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylic acid (1379691-07-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 0 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C

3.2: -78 °C

4.1: potassium tert-butylate; sodium hydride / tert-butyl alcohol / Reflux

With pyridine; n-butyllithium; potassium tert-butylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1002/chem.201102847

upstream raw materials:

ethyl 2-(4-methylbenzenesulfonyloxy)cyclohexanecarboxylate

cyclohex-1-enecarboxylic acid ethyl ester

(S)-N-benzyl-1-phenylethylamine

(1R,2S)-ethyl 2-(N-benzyl-N-((S)-α-methylbenzyl)amino)cyclohexanecarboxylate

Downstream raw materials:

(1S,2S)-2-(benzothiazol-2-ylamino)cyclohexylmethanol

(1S,2S)-2-amino-cyclohexylmethanol

rac-trans-2-aminocyclohexanecarboxylic acid