1-Methylpyrrolidine → HCID 131716120, compound

HRID 1607941Notes

Reaction equation

HRID 1607941 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:35](=[O:36])[N:11]2[C:12]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:13]([CH2:17][I:18])[CH2:14][S:15](=[O:16])[C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][N:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.C(OCC)(=O)C>CN(C)C=O>[I-:18].[C:1]([O:5][C:6]([NH:8][CH:9]1[C:35](=[O:36])[N:11]2[C:12]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:13]([CH2:17][N+:38]3([CH3:37])[CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:14][S:15](=[O:16])[C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 84541-MethylpyrrolidineHCID 8857Ethyl AcetateHCID 67833353HCID 67833353, compound

Product 1

HCID 131716120HCID 131716120, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzhydryl 7-tert-butoxycarbonylamino-3-iodomethyl-3-cephem-4-carboxylate-1-oxide (4.3 g) in dimethylformamide (70 ml) was added 1-methylpyrrolidine (0.63 g) at 0° C. The mixture was stirred for 1.5 hours under ice-cooling and poured into a mixture of ethyl acetate (700 ml) and ice-water (350 ml). The separated organic layer was washed with water, brine and dried over magnesium sulfate. The solvent was distilled off and the residue was pulverized in diisopropyl ether, collected by filtration and dried in vacuo to give powdery benzhydryl 7-tert-butoxycarbonylamino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate-1-oxide iodide (4.3 g).

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. filtrationcollected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-61ed03712c064721bd64396ef7582e0f
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

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