Carbonic Acid → 4-Methylmorpholine

HRID 1957038Notes

Reaction equation

HRID 1957038 reaction equation
[C:1](=[O:4])(O)O.C(Cl)(Cl)=O.[CH2:9]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH3:10].Cl[CH2:17]Cl.[C:19]1([CH3:25])[CH:24]=CC=CC=1>O1CCCC1.CCOCC.ClCCCl>[CH:14]([N:11]([CH2:12][CH3:13])[CH:19]([CH3:24])[CH3:25])([CH3:15])[CH3:17].[CH3:12][N:11]1[CH2:14][CH2:1][O:4][CH2:10][CH2:9]1

Participants

10

Reactant 5

HCID 767Carbonic AcidHCID 1140TolueneHCID 6344DichloromethaneHCID 6371PhosgeneHCID 8471Triethylamine

Product 2

HCID 79724-MethylmorpholineHCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In step d1, the compound (XIX) is reacted with a reactive derivative of carbonic acid, such as phosgene, in solution in toluene, or 1,1-carbonyldiimidazole, in the presence of a base such as triethylamine, N,N-diisopropylethylamine or N-methylmorpholine, in a chlorinated solvent such as dichloromethane or 1,2-dichloroethane, or an ether such as tetrahydrofuran, and at a temperature between -70° C. and room temperature, to give a compound of the expected formula (II) in which E is an O-protecting group.

Sources & evidence

ORD record
ord-b518d1731f09407296e0c9c58620cc90
Source dataset
uspto-grants-1998_07
Patent number
US05780466

Reaction notes

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