(3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine

Base Information

• Chemical Name: (3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine
• CAS No.: 1346681-95-5
• Molecular Formula: C₁₇H₂₅NO₂
• Molecular Weight: 275.391
• Mol file: 1346681-95-5.mol

Synonyms:

Chemical Property of (3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine

There total 2 articles about (3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine 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:

3-methylmorpholine (42185-06-8) + (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one (1346681-71-7) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl (3R)-3-methylmorpholine-4-carboxylate (1346681-94-4) + benzyl (3S)-3-methylmorpholine-4-carboxylate + (3R)-4-(3-mesitylpropanoyl)-3-methyl morpholine + (3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine (1346681-95-5)

Guidance literature:

3-methylmorpholine; (1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one; With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 23 ℃; for 18h; Inert atmosphere;

benzyl chloroformate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja209472h

Reference yield:

→ (3R)-4-(3-mesitylpropanoyl)-3-methyl morpholine + (3S)-4-(3-mesitylpropanoyl)-3-methyl morpholine (1346681-95-5)

Guidance literature:

With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 18h; Overall yield = 22 %; Overall yield = 15 mg; Optical yield = 58 %ee;

upstream raw materials:

3-methylmorpholine

(1E)-4-hydroxy-1-mesityl-4-methylpent-1-en-3-one

benzyl chloroformate

Refernces

• 1、 Binanzer, Michael,Hsieh, Sheng-Ying,Bode, Jeffrey W.. "Catalytic kinetic resolution of cyclic secondary amines". supporting information; experimental part. p. 19698 - 19701. Retrieved 2012/01/13.