Ethyl bromoacetate → Ethyl 5-benzyloxycarbonylamino-2-oxo-1-pyrrolidine-acetate

HRID 446126Notes

Reaction equation

HRID 446126 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[NH:16][C:15](=[O:17])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:16]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:15](=[O:17])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 126384645-Benzyloxycarbonylamino-2-pyrrolidone

Product 1

HCID 66713569Ethyl 5-benzyloxycarbonylamino-2-oxo-1-pyrrolidine-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

WO 93/09120 describes a process for the preparation of dimiracetam (2,5-dioxohexa-hydro-1H-pyrrolo[1,2-a]imidazole) 1 and related compounds. 5-Ethoxy-2-pyrrolidone is reacted with benzyl carbamate with a catalytic amount of p-toluenesulfonic acid to give 5-benzyloxycarbonylamino-2-pyrrolidone. This compound is then deprotonated at the pyrrolidine nitrogen with sodium hydride in acetonitrile, and reacted with ethyl bromoacetate to give ethyl 5-benzyloxycarbonylamino-2-oxo-1-pyrrolidine-acetate 2. Cyclization can then be performed after cleavage of the ethyl ester and/or the benzyloxycarbonyl protecting group in the presence of a variety of cyclizing agents.

Sources & evidence

ORD record
ord-37e5046e6c4d44eba1f439db0b30f85c
Source dataset
uspto-grants-2013_07
Patent number
US08476453B2

Reaction notes

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