3S-3-METHYLMORPHOLINE Chemical Properties

Boiling point:

137.1±15.0 °C(Predicted)

Density 

0.891±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.03±0.40(Predicted)

form 

liquid

color 

colourless

optical activity

Consistent with structure

InChI

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

InChIKey

SFWWGMKXCYLZEG-YFKPBYRVSA-N

SMILES

N1CCOC[C@@H]1C

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

2735

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

2934999090

3S-3-METHYLMORPHOLINE Usage And Synthesis

Uses

It is useful in preparation of morpholinopyrimidine derivatives as mTOR kinase inhibitors for the treatment of diseases mediated by mTOR kinase and/or one or more PI3K enzymes.

Uses

(3S)-3-Methylmorpholine is useful in preparation of morpholinopyrimidine derivatives as mTOR kinase inhibitors for the treatment of diseases mediated by mTOR kinase and/or one or more PI3K enzymes

Synthesis

Step-4: Synthesis of (S)-3-methylmorpholine (117): lithium aluminum hydride (87 g, 3.0 eq.) was suspended in anhydrous tetrahydrofuran (1500 mL) in a three necked round bottomed flask at 0°C under nitrogen protection. (S)-5-methylmorpholin-3-one (88 g) was dissolved in anhydrous tetrahydrofuran (500 mL) and slowly added dropwise to the reaction system at the same temperature. The reaction mixture was gradually warmed to room temperature and stirred continuously overnight. Upon completion of the reaction, it was quenched sequentially with water (100 mL), 2N sodium hydroxide solution (200 mL), and water (300 mL) (using Fisher post-treatment method) and stirred for 30 minutes. Subsequently, a 2% methanol/dichloromethane mixture (1000 mL) was added and stirring was continued for 1.0 hour. The crude product was filtered through a diatomaceous earth pad, and the filtrate was dried over anhydrous sodium sulfate and finally concentrated on a rotary evaporator at a low water bath temperature of 20-25 °C to afford the target product (S)-3-methylmorpholine (55 g, 71% yield).

References

[1] Patent: WO2014/16849, 2014, A2. Location in patent: Page/Page column 126; 127; 128
[2] Synthesis (Germany), 2014, vol. 46,
[3] Patent: US2008/255114, 2008, A1. Location in patent: Page/Page column 17
[4] Patent: EP1785418, 2007, A1. Location in patent: Page/Page column 148
[5] Patent: CN106749081, 2017, A. Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020; 0021

3S-3-METHYLMORPHOLINE(350595-57-2)Related Product Information

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• Anisodine
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• (-)-SCOPOLAMINE PERCHLORATE
• SCOPOLAMINE METHYL CHLORIDE, [N-METHYL-3H]