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Tetrabutylammonium Fluoride → (+/-)-2-Chloro-N-[{1-[(2-hydroxyethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide

HRID 20843
Notes
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Reaction equation

HRID 20843 reaction equation
[Cl:1][C:2]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][CH:7]([C:14]1([N:19]([CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCCCC>[Cl:1][C:2]1[C:34]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:32]=[CH:31][C:3]=1[C:4]([NH:6][CH:7]([C:14]1([N:19]([CH2:21][CH2:22][OH:23])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:5]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59347865(+)-2-Chloro-n-[{1-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide

Product 1

HCID 59347872(+/-)-2-Chloro-N-[{1-[(2-hydroxyethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 8003PentaneSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of (±)-2-chloro-N-[{1-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide D30 (0.390 g; 0.685 mmol) in THF (10 ml) was added tetrabutylammonium fluoride (1M solution in THF 1.6 ml; 1.6 mmol). The reaction mixture was allowed to stir at room temperature for 4 h. The desired product was isolated by column chromatography on silica using 20% to 50% ether in n-pentane, the solvent was reduced in volume by evaporation in vacuo and loaded onto an SCX cartridge. Washing with DCM, then methanol followed by elution with 1M ammonia in methanol afforded the title product (170 mg, 73%). Mass Spectrum (Electrospray LC/MS). Found 455 (MH+). C23H2635ClF3N2O2 requires 454. Ret. time: 2.09 min.

Sources & evidence

ORD record
ord-d50f960bff5b41df87c9c0d7b24ed7e1
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07745642B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes