Acetic Anhydride → Rolziracetam

HRID 978199

Reaction equation

HRID 978199 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.C(OC(=O)C)(=O)C.CC1OC(C)(C)OC(=O)C=1.C=C1OC(=O)C1>>[CH2:4]1[CH:5]2[N:6]([C:9](=[O:11])[CH2:8][CH2:7]2)[C:2](=[O:1])[CH2:3]1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 12661DiketeneHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 45856673-(5-Oxopyrrolidin-2-yl)propanoic acid

Product 1

HCID 71893Rolziracetam

Procedure

In a process for preparing dihydro-1H-pyrrolizine-3,5(2H, 6H)-dione comprising the steps of catalytically hydrogenating an ester of 4-(hydroxyimino)heptanedioic acid and subsequently cyclizing the resulting product to dihydro-1H-pyrrolizine-3,5(2H,6H)-dione, the improvement comprises reacting an alcoholic solution of a mono(lower alkyl) ester of 4-(hydroxyimino)heptanedioic acid, wherein lower alkyl comprises from one to three carbon atoms, with hydrogen gas at a temperature of about 60° C. in the presence of rhodium/alumina catalyst and a tertiary lower alkyl amine, wherein said lower alkyl amine comprises from three to nine carbon atoms, to produce 5-oxo-2-pyrrolidinepropanoic acid; and thereafter heating said 5-oxo-2-pyrrolidinepropanoic acid in the presence of a cyclizing agent selected from acetic anhydride, 2,2,6-trimethyl-1,3-dioxen-4-one, and diketene at a temperature of about 90° C. to produce dihydro-1H-pyrrolizine-3,5(2H,6H)-dione.

Workup

  1. temperatureand thereafter heating

Sources & evidence

ORD record
ord-a0894d6580a741cba8f872bfbd9b211b
Source dataset
uspto-grants-1987_05
Patent number
US04663464

Linked notes

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