Tetrabutylammonium Fluoride → [(R)-1-(4-Hydroxy-phenyl)-2-(4-methyl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 454981Notes

Reaction equation

HRID 454981 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([C:17]1[CH:22]=[CH:21][C:20]([O:23][Si](C(C)(C)C)(C)C)=[CH:19][CH:18]=1)[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOCC>[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)[CH2:9][N:10]1[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67073781[(R)-1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-(4-methyl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 58459801[(R)-1-(4-Hydroxy-phenyl)-2-(4-methyl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(R)-1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-(4-methyl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester (370 mg, 0.82 mmol) in THF (3 ml) was added TBAF (1M in THF, 1 ml, 1 mmol). The resulting mixture was stirred at rt for 3 h. The reaction mixture was diluted with ether and quenched with aq. NH4Cl. The organic layer was washed with water and brine, and then dried over MgSO4. Removal of the solvent provided the titled compound.

Workup

  1. customquenched with aq. NH4Cl
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-2d4a43c6f3f14a4b88b27534034d37c4
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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