Ethyl bromoacetate → 4-[2-(Carboxy)-ethyl]-1-[(cyclohexyloxycarbonyl)-methyl]-pipe-ridine

HRID 581841Notes

Reaction equation

HRID 581841 reaction equation
Br[CH2:2][C:3]([O:5]CC)=[O:4].Br[CH2:9][C:10]([O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11].Br[CH2:20]C(Cl)=O.C1(O)CCCCC1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>CN(C)C1C=CN=CC=1>[C:3]([CH2:2][CH2:20][CH:34]1[CH2:35][CH2:36][N:31]([CH2:9][C:10]([O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:11])[CH2:32][CH2:33]1)([OH:5])=[O:4]

Participants

7

Reactant 5

HCID 7748Ethyl bromoacetateHCID 7966CyclohexanolHCID 89602Bromoacetyl chlorideHCID 221279Cyclohexyl bromoacetateHCID 21992828Pyridine ethyl acetate

Product 1

HCID 211985324-[2-(Carboxy)-ethyl]-1-[(cyclohexyloxycarbonyl)-methyl]-pipe-ridine

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The preparation is carried out analogously to Examples XLIIa to c. Instead of ethyl bromoacetate, cyclohexyl bromoacetate (boiling point: 102-104° C. under 16 mbar, prepared by reaction of bromoacetyl chloride with cyclohexanol in pyridine/ethyl acetate in the presence of a catalytic amount of 4-dimethylaminopyridine) is employed. Melting point: 85-88° C.

Sources & evidence

ORD record
ord-5088b1b3b0764c0590b0d72d77f1131b
Source dataset
uspto-grants-1999_07
Patent number
US05922717

Reaction notes

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