ChemicalBook CAS DataBase List (R)-3-Methylmorpholine

(R)-3-Methylmorpholine synthesis

8synthesis methods

Product Name:(R)-3-Methylmorpholine
CAS Number:74572-04-6
Molecular formula:C5H11NO
Molecular Weight:101.15

119844-67-6

74572-04-6

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.

119844-67-6
50 suppliers
$90.00/50mg

74572-04-6
187 suppliers
$10.00/250mg

Yield:74572-04-6 75%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 16 h;

Steps:

General Procedure for synthesis of 5:
General procedure: LAH (2 equiv.) in THF (100 mL) was cooled to 0oC inan ice bath under nitrogen. A solution of 4 (1 equiv.) in THF (20 mL) was added dropwise, and the resulting solution was stirred at RT for 16 hrs. The reaction mixture was cooled to 0oC andcarefully quenched with water (2 mL), 2 N NaOH (2 mL) and water (8 mL). The resulting slurrywas stirred at RT for 1 h and filtered through Celite. The filter cake was washed with ethylacetate and discarded. The filtrate was dried (Na2SO4), separated and concentrated to afford 5 asa colorless oil.

References:

Dugar, Sundeep;Sharma, Amit;Kuila, Bilash;Mahajan, Dinesh;Dwivedi, Sandeep;Tripathi, Vinayak [Synthesis,2014,vol. 46,art. no. 46] Location in patent:supporting information

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74571-98-5 Synthesis