Tetrabutylammonium Fluoride → HCID 21192932, compound

HRID 1067292Notes

Reaction equation

HRID 1067292 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([Cl:36])[C:15]([NH:21][C:22](=[O:35])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:31]([F:34])([F:33])[F:32])[CH:24]=3)=[CH:16][CH:17]=2)[CH2:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:9][CH2:10][N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[C:14]([Cl:36])[C:15]([NH:21][C:22](=[O:35])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([C:31]([F:32])([F:34])[F:33])[CH:24]=3)=[CH:16][CH:17]=2)[CH2:12]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21192931HCID 21192931, compound

Product 1

HCID 21192932HCID 21192932, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

N-(2-(2-Tert-butyldimethylsilyloxyethyl)-8-chloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methoxy-3-trifluoromethylbenzamide (0.09 g) in tetrahydrofuran (10 ml) was treated with tetrabutylammonium fluoride in tetrahydrofuran (1M, 0.16 ml) at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water, the organic phase dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, ammonia/methanol/dichloromethane mixtures as eluant) to give the title compound (0.04 g)

Workup

  1. washwashed with water
  2. dry with materialthe organic phase dried (MgSO4) and solvent
  3. customremoved at reduced pressure
  4. customchromatographed (silica gel, ammonia/methanol/dichloromethane mixtures as eluant)

Sources & evidence

ORD record
ord-085c965a3c0f477393df59a5dc721623
Source dataset
uspto-grants-2001_06
Patent number
US06248754B1

Reaction notes

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