(R)-3-Methylmorpholine Chemical Properties

Boiling point:

137.1±15.0 °C(Predicted)

Density 

0.891±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

9.03±0.40(Predicted)

form 

liquid

color 

Colourless

InChI

InChI=1S/C5H11NO/c1-5-4-7-3-2-6-5/h5-6H,2-4H2,1H3/t5-/m1/s1

InChIKey

SFWWGMKXCYLZEG-RXMQYKEDSA-N

SMILES

N1CCOC[C@H]1C

Safety Information

HS Code 

2934999090

(R)-3-Methylmorpholine Usage And Synthesis

Chemical Properties

colourless liquid

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.

Synthesis

GENERAL STEPS: A tetrahydrofuran (THF, 100 mL) solution of lithium aluminum hydride (LAH, 2 eq.) was cooled to 0 °C in an ice bath under nitrogen protection. A solution of (R)-5-methylmorpholin-3-one (1 eq.) in THF (20 mL) was slowly added dropwise. After the dropwise addition, the reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the mixture was cooled again to 0 °C and quenched by careful addition of water (2 mL), 2N sodium hydroxide solution (2 mL) and water (8 mL) in that order. After quenching, the resulting slurry was stirred at room temperature for 1 hour and then filtered through diatomaceous earth. The filter cake was washed with ethyl acetate and discarded. The filtrate was dried with anhydrous sodium sulfate, separated and concentrated to give (R)-3-methylmorpholine as a colorless oil.

References

[1] Synthesis (Germany), 2014, vol. 46,
[2] Patent: EP1785418, 2007, A1. Location in patent: Page/Page column 149

(R)-3-Methylmorpholine(74572-04-6)Related Product Information

• Benzyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• Naxagolide
• Methscopolamine bromide
• Scopolamine hydrobromide
• (5R)-3,4,5,6-Tetrahydro-5-phenyl-4(H)-1,4-oxazin-2-one
• HYOSCINE HYDROCHLORIDE
• Scopolamine butylbromide
• Voxergolide
• SCOPOLAMINE METHYL NITRATE
• SCOPOLAMINE N-OXIDE HYDROBROMIDE
• Anisodine hydrobromide
• Scopine hydrochloride
• tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• APOHYOSCINE
• (+)-(4aR,10bR)-3,4,4a,10b-Tetrahydro-4-propyl-2H,5H-[1]benzopyrano[4,3-b]-1,4-oxazin-9-ol hydrochloride
• Anisodine
• (-)-SCOPOLAMINE PERCHLORATE
• SCOPOLAMINE METHYL CHLORIDE, [N-METHYL-3H]