Tetrabutylammonium Fluoride → HCID 22903694, compound

HRID 1489161Notes

Reaction equation

HRID 1489161 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][N:20]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH2:13]OS(C)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:35].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][N:20]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH2:13][F:35])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22903691HCID 22903691, compound

Product 1

HCID 22903694HCID 22903694, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-3-(dibenzylaminomethyl)-3-mesyloxymethylpyrrolidine (6.90 g) in acetonitrile (70 ml) was added to 1N tetrabutylammonium fluoride in tetrahydrofuran (72 ml), and the mixture was starred at 40° C. for 16 hours. After concentration, the concentrate was poured into water (200 ml), and the mixture was made alkaline with aqueous ammonia and extracted with ether. The ether layer was washed with water, dried, concentrated and purified by silica gel column chromatography to give 4.37 g of the object compound as an oil.

Workup

  1. concentrationAfter concentration
  2. additionthe concentrate was poured into water (200 ml)
  3. extractionextracted with ether
  4. washThe ether layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-165aed790ecc4969b6810eb4ab581902
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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