74572-13-7

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

• 74572-10-4 (2S)-2-methyl-4-tosyl-morpholine 
• 120800-89-7 (S)-4-benzyl-2-methylmorpholine 
• 454251-71-9 (2S,4aS,7R,8aR)-N-allyl-2-hydroxymethyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 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 
• 74572-07-9 (S)-1-((2-hydroxyethyl)amino)propan-2-ol 
• 127958-63-8 (S)-6-methyl-3-morpholinone 

Downstream Products

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

Relevant academic research and scientific papers

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.

Preparation method of chiral morpholine compound

The invention provides a preparation method of a chiral morpholine compound. With chiral ethylene oxide as a raw material, the preparation method comprises the steps of ring opening, cyclization and deprotection reaction to obtain the chiral 2-substituted morpholine compound. The preparation process is simple and environmentally friendly, has mild reaction conditions, is free of irritation or allergens, has higher total yield and good safety and is suitable for industrial amplification.

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.

DIBENZOTHIOPHENE DERIVATIVES AS DNA- PK INHIBITORS

Compound formula I: wherein: X1 and X2 may be either (a) C and O, (b) N and N, or (c) C and NH, where the dotted bonds represents a double bond in the appropriate location; R1 and R2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; RN1 is selected from hydrogen and an optionally substituted C1-4 alkyl group; RC1 is selected from an optionally substituted C1-7 alkyl group, an optionally substituted C3-20 heterocyclyl group, or an optionally substituted C5-20 aryl group; or RN1 and RC1 may together form an optionally substituted C2-4 alkylene group.

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.

SYNTHESIS AND ABSOLUTE CONFIGURATION OF SUBSTITUTED MORPHOLINES

We studied methods of stereospecific synthesis that enabled us to obtain variously substituted morpholinic compounds and to determine their absolute configuration.From a study of the chiroptical properties of synthetic N-(2-pyridyl-N-oxide) derivatives of optically active morpholines, it was possible to correlate the sign of the Cotton effect with the absolute configuration.This correlation agrees with that previously established for derivatives of the piperidine type.By evaluating the various contributions to the Cotton effect of substituents in positions 2 and 3, we established the absolute configuration of bicyclic compounds condensed in the two positions mentioned above.