Ethanol → 3-hydroxyaniracetam

HRID 1462941Notes

Reaction equation

HRID 1462941 reaction equation
COC1C=CC(C(N2CCC([C@@H](Cl)C([O-])=O)C2=O)=O)=CC=1.NC(N)=S.C(O)C.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]([N:39]2[C:43](=[O:44])[CH:42]([OH:45])[CH2:41][CH2:40]2)=[O:38])=[CH:33][CH:32]=1>N1C=CC=CC=1.CCOCC.C(OCC)(=O)C>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]([N:39]2[CH2:40][CH2:41][C@@H:42]([OH:45])[C:43]2=[O:44])=[O:38])=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 2723790ThioureaHCID 30608043-Hydroxy-1-(4-methoxybenzoyl)pyrrolidin-2-oneHCID 86739567HCID 86739567, compound

Product 1

HCID 1741273-hydroxyaniracetam

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.0 g of (R)-1-(p-methoxybenzoyl)-2-oxo-3-pyrrolidinyl-chloroacetate are treated in pyridine with thiourea and ethanol according to the procedure described in paragraph (c) of Example 5; the reaction time amounting to 45 minutes. The residue obtained after working-up the ethyl acetate extracts is stirred in ether, the insoluble constituents being filtered off and recrystallised from diisopropyl ether. There is obtained (R)-1-(p-methoxybenzoyl)-3-hydroxy-2-pyrrolidinone of melting point 123°-124° C.; [α]D20 =+214°; [α]54620 =+264°; [α]36520 =+1212° (c=1.0 in chloroform).

Workup

  1. customThe residue obtained
  2. filtrationthe insoluble constituents being filtered off
  3. customrecrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-e6e3b351c7084c90ab01ac179150b8f6
Source dataset
uspto-grants-1984_07
Patent number
US04461906

Reaction notes

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