Dimethyl Sulfate → HCID 14666748, compound

HRID 648558Notes

Reaction equation

HRID 648558 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:14]=[CH:13][N:12]3[C:7](=[C:8]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][C@@H:25]4[CH2:29][OH:30])=[O:23])[CH:9]=[C:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:11]3=[O:15])[C:6]=2[CH:31]=1.[OH-].[Na+].S(OC)(O[CH3:38])(=O)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:14]=[CH:13][N:12]3[C:7](=[C:8]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][C@@H:25]4[CH2:29][O:30][CH3:38])=[O:23])[CH:9]=[C:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:11]3=[O:15])[C:6]=2[CH:31]=1

Participants

7

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium HydroxideHCID 3035058Ro 19-8022

Product 1

HCID 14666748HCID 14666748, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

432 mg of (R)-1-[(10-chloro-4-oxo-3-phenyl-4H-benzo[a]quinolizin-1-yl)carbonyl]-2-pyrrolidinemethanol and 4 mg of tetrabutylammonium iodide in 2 ml of methylene chloride were held in an ultrasound bath for 30 minutes with 104 mg of sodium hydroxide in 0.1 ml of water. 0.19 ml of dimethyl sulfate was then added. After about 1 hour, an additional 0.19 ml of dimethyl sulfate was added and the mixture was allowed to react for an additional 90 minutes. The mixture was diluted with methylene chloride, washed with water, dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on silica gel and the product was recrystallized from cyclohexane/ethanol. There was obtained (R)-1-[(10-chloro-4-oxo-3-phenyl-4H-benzo[a]quinolizin-1-yl)carbonyl]-2-methoxymethylpyrrolidine as yellow crystals of m.p. 137°-140°.

Workup

  1. customto react for an additional 90 minutes
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. customthe product was recrystallized from cyclohexane/ethanol

Sources & evidence

ORD record
ord-ddf2c6f8cbaf49ae9b259818a61b804a
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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