| Identification | Back Directory | [Name]
(R)-3-Methylmorpholine | [CAS]
74572-04-6 | [Synonyms]
(R)-3-MethyL
(R)-3-Methylmorpholine
elagolix intermediate 8
Morpholine, 3-methyl-, (R)-
Morpholine, 3-Methyl-, (3R)-
(R)-3-Methylmorpholine(WX900060)
(R)-3-MethylmorpholineortheHClsalt | [Molecular Formula]
C5H11NO | [MDL Number]
MFCD10698482 | [MOL File]
74572-04-6.mol | [Molecular Weight]
101.15 |
| Chemical Properties | Back Directory | [Boiling point ]
137.1±15.0 °C(Predicted) | [density ]
0.891±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [form ]
liquid | [pka]
9.03±0.40(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
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