4-Hydroxypyrrolidine → HCID 13520242, compound

HRID 485083Notes

Reaction equation

HRID 485083 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.F[C:8]1[C:19]2=[C:20]3[N:15]([C:16](=[CH2:21])[CH2:17][CH2:18]2)[CH:14]=[C:13]([C:22]([OH:24])=[O:23])[C:12](=[O:25])[C:11]3=[CH:10][C:9]=1[F:26]>CS(C)=O>[F:26][C:9]1[CH:10]=[C:11]2[C:20]3[N:15]([CH:14]=[C:13]([C:22]([OH:24])=[O:23])[C:12]2=[O:25])[C:16](=[CH2:21])[CH2:17][CH2:18][C:19]=3[C:8]=1[N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[CH2:3]1

Participants

4

Reactant 2

HCID 982104-HydroxypyrrolidineHCID 13373748HCID 13373748, compound

Product 1

HCID 13520242HCID 13520242, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4 ml of dimethyl sulfoxide and 100 mg of 3-hydroxypyrrolidine were added to 100 mg of 8,9-difluoro-5-methylene-1-oxo-6,7-dihydro-1H,5H-benzo(ij)quinolizine-2-carboxylic acid and the resulting mixture was allowed to react for 2 hours at 120° C. The solvent was distilled off. The residue was purified by silica gel column chromatography and purified by preparative thin layer chromatography on silica gel and then recrystallized from a mixture of ethanol and chloroform to give 28 mg of 9-fluoro-8-(3-hydroxy-1-pyrrolidinyl)-5-methylene-1-oxo-6,7-dihydro-1H,5H-benzo(ij)quinolizine-2-carboxylic acid as microcrystals with mp 190°-196° C.

Workup

  1. customto react for 2 hours at 120° C
  2. distillationThe solvent was distilled off
  3. customThe residue was purified by silica gel column chromatography
  4. custompurified by preparative thin layer chromatography on silica gel
  5. customrecrystallized from a mixture of ethanol and chloroform

Sources & evidence

ORD record
ord-a094037dd0434397939cc89317d5c1b8
Source dataset
uspto-grants-1985_08
Patent number
US04535161

Reaction notes

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