2-Benzyloxy-3-hexadecyloxypropyl 1,1-dimethylpyrrolidinio-2-ylmethyl phosphate → 3-Hexadecyloxy-2-hydroxypropyl 1,1-dimethylpyrrolidinio-2-ylmethyl phosphate

HRID 2081494Notes

Reaction equation

HRID 2081494 reaction equation
[P:1]([O-:41])([O:32][CH:33]=[C:34]1[CH2:38][CH2:37][CH2:36][N+:35]1([CH3:40])[CH3:39])([O:3][CH2:4][CH:5]([O:24]CC1C=CC=CC=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][CH3:23])=[O:2].[H][H]>C(O)C.[Pd]>[P:1]([O-:41])([O:32][CH:33]=[C:34]1[CH2:38][CH2:37][CH2:36][N+:35]1([CH3:40])[CH3:39])([O:3][CH2:4][CH:5]([OH:24])[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][CH3:23])=[O:2]

Participants

5

Reactant 2

HCID 1317166502-Benzyloxy-3-hexadecyloxypropyl 1,1-dimethylpyrrolidinio-2-ylmethyl phosphateHCID 178418361HCID 178418361, compound

Product 1

HCID 1317166523-Hexadecyloxy-2-hydroxypropyl 1,1-dimethylpyrrolidinio-2-ylmethyl phosphateYield 80.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 162 mg of 2-Benzyloxy-3-hexadecyloxypropyl 1,1-dimethylpyrrolidinio-2-ylmethyl phosphate prepared in Example 7, and 20 mg of palladium(5%)-carbon (catalyst) was added to the resulting solution. The mixture was stirred overnight at 50° C. in a stream of hydrogen. The reaction liquid was cooled, and the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure to give 111 mg of 3-hexadecyloxy-2-hydroxypropyl 1,1-dimethylpyrrolidinio-2-ylmethyl phosphate.

Workup

  1. additionwas added to the resulting solution
  2. customThe reaction liquid
  3. temperaturewas cooled
  4. customthe catalyst was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e1ada460f72e4fa1ba08a1b9042053e2
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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