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

HRID 20843
ノート
印刷プレビュー

反応式

HRID 20843 の反応式
[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]
参加物実験手順出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-d50f960bff5b41df87c9c0d7b24ed7e1
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07745642B2

反応ノート

読み込み中…

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