Tetrabutylammonium Fluoride → HCID 12085945, compound

HRID 397079Notes

Reaction equation

HRID 397079 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[CH:33]([C:37]2[CH:42]=[CH:41][C:40]([O:43]S(C4C=CC(C)=CC=4)(=O)=O)=[CH:39][CH:38]=2)[N:32]([C:54](=[O:59])[C:55]([F:58])([F:57])[F:56])[CH2:31][CH2:30]3)[CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1>[F:57][C:55]([F:56])([F:58])[C:54]([N:32]1[CH2:31][CH2:30][C:29]2[C:34](=[CH:35][CH:36]=[C:27]([O:26][CH2:25][CH2:24][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:28]=2)[CH:33]1[C:37]1[CH:38]=[CH:39][C:40]([OH:43])=[CH:41][CH:42]=1)=[O:59]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86583959HCID 86583959, compound

Product 1

HCID 12085945HCID 12085945, compoundYield 183.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1M TBAF in THF (2.8 ml, 2.82 mmol) and toluene-4-sulfonic acid 4-[6-(2-pyrrolidin-1-yl-ethoxy)-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-1-yl]phenyl ester (0.415 g, 0.71 mmol) in anhydrous THF (50 ml) was refluxed under N2 for 18 hr, then concentrated in vacuo to a green oil. This was suspended in sat. NaHCO3 solution (25 ml), then extracted with EtOAc (3×40 ml). The combined extracts were dried over MgSO4 and concentrated in vacuo to give 0.566 g of green oil. Purification by flash chromatography, eluting with EtOAc:MeOH (8:2) gave 0.241 g (79% yield) of yellow oil.

Workup

  1. concentrationconcentrated in vacuo to a green oil
  2. extractionextracted with EtOAc (3×40 ml)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7425af4a4ae049a095f8b6009608187c
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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