1-Methylpyrrolidine → HCID 70400873, compound

HRID 986186Notes

Reaction equation

HRID 986186 reaction equation
[P:1]([O-:38])([O:34][CH2:35][CH2:36]Br)([O:3][CH2:4][CH:5]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2].[CH3:39][N:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[P:1]([O-:38])([O:34][CH2:35][CH2:36][N+:40]1([CH3:39])[CH2:44][CH2:43][CH2:42][CH2:41]1)([O:3][CH2:4][CH:5]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:2]

Participants

5

Reactant 2

HCID 84541-MethylpyrrolidineHCID 86741914HCID 86741914, compound

Product 1

HCID 70400873HCID 70400873, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

In 30 ml of toluene were dissolved 7.5 g (12 mmole) of 2-benzyloxy-3-(octadecyloxy)propyl 2-bromoethyl phosphate and 10.2 g (120 mmole) of N-methylpyrrolidine, and the solution was allowed to stand at room temperature for 8 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in 60 ml of methanol. 3.3 g (12 mmole) of silver carbonate was added to the solution, followed by heating under reflux for 1 hour. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol:water=65:25:4) to give 3.5 g (47 %) of 2-benzyloxy-3-(octadecyloxy)-propyl 2-(N-methylpyrrolidinio)ethyl phosphate.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in 60 ml of methanol
  3. temperatureby heating
  4. temperatureunder reflux for 1 hour
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol:water=65:25:4)

Sources & evidence

ORD record
ord-743f23768e31439a9f2e54f0adb60c25
Source dataset
uspto-grants-1987_12
Patent number
US04710579

Reaction notes

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