Trimethylsilyl iodide → 7-[3-(Butoxycarbonyl)amino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 483291Notes

Reaction equation

HRID 483291 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:17])[C:6]([C:18]([O:20]C)=[O:19])=[CH:5]2)[CH2:3][CH2:2]1.I[Si](C)(C)C.C(=O)(O)O.[CH2:31]([O:35][C:36]([NH:38][CH:39]1[CH2:43][CH2:42][NH:41][CH2:40]1)=[O:37])[CH2:32][CH2:33][CH3:34]>ClCCl.C(#N)C>[CH2:31]([O:35][C:36]([NH:38][CH:39]1[CH2:43][CH2:42][N:41]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:17])[C:6]([C:18]([OH:20])=[O:19])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:16])[CH2:40]1)=[O:37])[CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 13590045Methyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateHCID 202428763-Butoxycarbonylaminopyrrolidine bicarbonate

Product 1

HCID 135900477-[3-(Butoxycarbonyl)amino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 82.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g (3.4 mmole) of methyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 25 ml dichloromethane was added 0.6 ml (0.8 g, 4.2 mmole) of iodotrimethylsilane while stirring at room temperature under a nitrogen atmosphere. The mixture was warmed to reflux and stirred overnight. The reaction was cooled to room temperature, concentrated, and the residue taken up in 25 ml acetonitrile. To the resulting suspension was added a solution of 1.6 g (8.5 mmole) of 3-butoxycarbonylaminopyrrolidine bicarbonate in 10 ml acetonitrile while under nitrogen. The reaction was warmed to reflux for four hours, then cooled to room temperature. The formed precipitate was filtered, washed with acetonitrile and ether, yielding 1.26 g (82%) of 7-[3-(butoxycarbonyl)amino-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 228°-230° C.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. stirringstirred overnight
  4. temperatureThe reaction was cooled to room temperature
  5. concentrationconcentrated
  6. temperatureThe reaction was warmed
  7. temperatureto reflux for four hours
  8. temperaturecooled to room temperature
  9. filtrationThe formed precipitate was filtered
  10. washwashed with acetonitrile and ether

Sources & evidence

ORD record
ord-311d3045bb5b48d5906a463369469790
Source dataset
uspto-grants-1986_03
Patent number
US04578473

Reaction notes

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