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Tetrabutylammonium Fluoride → Methyl 3-[[6-[3-(hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate

HRID 239965
ノート
印刷プレビュー

反応式

HRID 239965 の反応式
[Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:21]=[C:20]([C:22]([NH:24][C:25]3[C:26]([CH3:36])=[C:27]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:28]([O:30][CH3:31])=[O:29])=[O:23])[C:19]([CH3:37])=[CH:18][CH:17]=2)[CH2:11]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:21]=[C:20]([C:22]([NH:24][C:25]3[C:26]([CH3:36])=[C:27]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:28]([O:30][CH3:31])=[O:29])=[O:23])[C:19]([CH3:37])=[CH:18][CH:17]=2)[CH2:11]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707348Methyl 3-[[6-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate

生成物 1

HCID 86707349Methyl 3-[[6-[3-(hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate収率 115.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of methyl 3-[[6-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate (0.20 g, 0.38 mmol) in THF (4 ml) is added Bu4NF 1.0 M in THF (1.5 ml) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 8 hours, the reaction mixture is diluted with ice-water and extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (neutral alumina) over a gradient using 50% ethyl acetate in hexane to afford the title compound as a white solid (0.18 g, 115%). Mass spectrum (m/z): 412.2 (M+1).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by flash chromatography (neutral alumina) over a gradient

出典と根拠

ORDレコード
ord-6feb590cc3a346b080fece3f38c0ac32
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642768B2

反応ノート

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