Morpholine → HCID 14978394, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH3:12])[C:9]([OH:11])=O.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH3:12])[C:9]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To (2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionic acid (29.5 g) was added anhydrous tetrahydrofuran (250 ml). To the mixture was added, with stirring at room temperature, 1,1-carbonyldiimidazole (33.1 g), taking 10 minutes. The mixture was stirred for 30 minutes at room temperature and cooled with ice, to which was added dropwise morpholine (34.8 g) during 15 minutes. The resultant mixture was stirred for 15 minutes on an ice bath, then the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in dichloromethane (300 ml), which was washed with a saturated aqueous sodium chloride solution (50 ml) and dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel chromatography (eluent:hexane:ethyl acetate=1:4) to afford N-[(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine (17.5 g).