(R)-3-Methylmorpholine

Base Information

• Chemical Name: (R)-3-Methylmorpholine
• CAS No.: 74572-04-6
• Molecular Formula: C5H11NO
• Molecular Weight: 101.148
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40348918
• Nikkaji Number: J3.148.979B
• Wikidata: Q72493187
• Mol file: 74572-04-6.mol

Synonyms:(R)-3-METHYLMORPHOLINE;74572-04-6;(3R)-3-methylmorpholine;(R)-3-Methyl-morpholine;Morpholine, 3-methyl-, (3R)-;MFCD10698482;3-(R)-methylmorpholine;SCHEMBL306399;DTXSID40348918;CS-D1634;AKOS015840257;GS-4508;AC-22431;AM804311;A9544;J-502222;J-502453;J-512916

Chemical Property of (R)-3-Methylmorpholine

Chemical Property:

• Vapor Pressure: 7.14mmHg at 25°C
• Refractive Index: 1.409
• Boiling Point: 137.1 °C at 760 mmHg
• PKA: 9.03±0.40(Predicted)
• Flash Point: 41.3 °C
• PSA: 21.26000
• Density: 0.891 g/cm³
• LogP: 0.32350
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 101.084063974
• Heavy Atom Count: 7
• Complexity: 56

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-3-Methylmorpholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1COCCN1
• Isomeric SMILES: C[C@@H]1COCCN1
• Uses: (R)-3-Methylmorpholine is useful for the discovery of (2S)-8-[(3R)-3-Methylmorpholin-4-yl]-1-(3-methyl-2-oxobutyl)-2-(trifluoromethyl)-3,4-dihydro-2H-pyrimido[1,2-a]pyrimidin-6-one, an inhibitor of Vps34 for the treatment of solid tumors.

Technology Process of (R)-3-Methylmorpholine

There total 14 articles about (R)-3-Methylmorpholine 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: 83.0%

(R)-4-(4-methoxybenzyl)-3-methylmorpholine (954133-47-2) → (3R)-3-methylmorpholine (74572-04-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 50 ℃; for 18h; under 9500.64 Torr;

Reference yield: 75.0%

(5R)-5-methylmorpholin-3-one (119844-67-6) → (3R)-3-methylmorpholine (74572-04-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 16h;

DOI:10.1055/s-0034-1379641

Reference yield: 65.0%

(R)-2-(2-hydroxyethylamino)propan-1-ol → (3R)-3-methylmorpholine (74572-04-6)

Guidance literature:

(R)-2-(2-hydroxyethylamino)propan-1-ol; With sulfuric acid; at 140 ℃; for 14h;

With sodium hydroxide; In water; at 0 ℃;

upstream raw materials:

(3R)-3-methyl-4-(phenylmethyl)morpholine

(R)-2-[Benzyl-(2-hydroxy-ethyl)-amino]-propan-1-ol

(5R)-5-methylmorpholin-3-one

2-(prop-2-yn-1-yloxy)ethan-1-amine

Downstream raw materials:

8-benzyl-3-[(3R)-3-methylmorpholin-4-yl]-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

(6S)-8-benzyl-6-methyl-3-[(3R)-3-methylmorpholin-4-yl]-6,7,8,9-tetrahydropyrazino[2,3-f][1,4]oxazepine

(3R)-4-[2-chloro-6-[(methylsulfanyl)methyl]pyrimidin-4-yl]-3-methylmorpholine

(R)-3-methyl-4-tosylmorpholine

Refernces

• 1、 Lau, Ying Yin,Zhai, Huimin,Schafer, Laurel L.. "Catalytic Asymmetric Synthesis of Morpholines. Using Mechanistic Insights to Realize the Enantioselective Synthesis of Piperazines". . p. 8696 - 8709. Retrieved 2016/10/14.
• 2、 Allen, Scott E.,Hsieh, Sheng-Ying,Gutierrez, Osvaldo,Bode, Jeffrey W.,Kozlowski, Marisa C.. "Concerted amidation of activated esters: Reaction path and origins of selectivity in the kinetic resolution of cyclic amines via N-heterocyclic carbenes and hydroxamic acid cocatalyzed acyl transfer". . p. 11783 - 11791. Retrieved 2014/11/08.