74572-13-7

Basic information

• Product Name: (S)-2-Methyl-morpholine
• Synonyms: (S)-2-Methyl-morpholine;(S)-2-Methylmorpholine HCl;Morpholine, 2-Methyl-, (S)-;(2S)-2-MethylMorpholine;Morpholine, 2-methyl-, (2S)-
• CAS NO: 74572-13-7
• Molecular Formula: C₅H₁₁NO
• Molecular Weight: 101.14694
• Mol File: 74572-13-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 137℃
• Flash Point: 41℃
• Appearance: /
• Density: 0.891
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.01±0.40(Predicted)
• CAS DataBase Reference: (S)-2-Methyl-morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Methyl-morpholine(74572-13-7)
• EPA Substance Registry System: (S)-2-Methyl-morpholine(74572-13-7)

Safety Data

• RIDADR: 1993
• HazardClass: 3
• PackingGroup: Ⅲ
• Hazardous Substances Data: 74572-13-7(Hazardous Substances Data)

Usage

Uses

(S)-2-Methylmorpholine is a reactant in the synthesis of imidazo[1,2-a]-pyrimidin-5(1H)-ones as PI3K-beta selective inhibitors.

InChI:InChI=1/C5H11NO/c1-5-4-6-2-3-7-5/h5-6H,2-4H2,1H3/t5-/m0/s1

Upstream product

• 120800-89-7 (S)-4-benzyl-2-methylmorpholine 
• 127958-63-8 (S)-6-methyl-3-morpholinone 
• 914359-78-7 (3R,6aS,9R,10aR,11aS)-3-phenylselenenylmethyl-6,6,9-trimethyl-decahydro-3H,7H-[1,4]oxazino[3,4-b][1,3]benzoxazine 
• 914360-07-9 (2S)-4-(8-mentholyl)-2-methyl-morpholine 
• 914359-94-7 (3S,6aS,9R,10aR,11aS)-3,6,6,9-tetramethyl-decahydro-3H,7H-[1,4]oxazino[3,4-b][1,3]benzoxazine 
• 74572-10-4 (2S)-2-methyl-4-tosyl-morpholine 
• 454251-71-9 (2S,4aS,7R,8aR)-N-allyl-2-hydroxymethyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 74572-07-9 (S)-1-((2-hydroxyethyl)amino)propan-2-ol 

Downstream Products

• 74572-10-4 (2S)-2-methyl-4-tosyl-morpholine 

Relevant articles and documents

Formal Deoxygenative Hydrogenation of Lactams Using PNHP-Pincer Ruthenium Complexes under Nonacidic Conditions

A formal deoxygenative hydrogenation of amides to amines with RuCl2(NHC)(PNHP) (NHC = 1,3-dimethylimizadol-2-ylidene, PNHP = bis(2-diphenylphosphinoethyl)amine) is described. Various secondary amides, especially NH-lactams, are reduced with H2 (3.0-5.0 MPa) to amines at a temperature range of 120-150 °C with 1.0-2.0 mol % of PNHP-Ru catalysts in the presence of Cs2CO3. This process consists of (1) deaminative hydrogenation of secondary amides to generate primary amines and alcohols, (2) dehydrogenative coupling of the transient amines with alcohols to generate imines, and (3) hydrogenation of imines to give the formally deoxygenated secondary amine products.

A concise and efficient synthesis of substituted morpholines

A simple and efficient method has been developed for the synthesis of substituted morpholines by a sequence of coupling, cyclization, and reduction reactions of easily available amino alcohols and α-halo acid chlorides. Various mono-, di-, and trisubstituted morpholines, spiro morpholines, and ring-fused morpholines, as well as morpholine homologues, were synthesized in good to excellent yields by a single methodology under similar reaction conditions. The method was also used in a multigram synthesis of (3S)-3-methylmorpholine.

Diastereoselective synthesis of enantiopure morphelines by electrophilic selenium-induced 6-exo cyclizations on chiral 3-allyl-2-hydroxymethylperhydro-1, 3-benzoxazine derivatives

Enantiopure morpholine derivatives have been prepared by selenocyclofunctionalization of chiral 3-allyl-2-hydroxymethyl-substituted perhydro-1,3-benzoxazine derivatives. The cyclization occurs in high yields and diastereoselection, although the temperature of the reaction and the structure of the substituent at C-2 and the substitution pattern of the double bond can modify the regio- and stereochemistry of the final products.