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

HRID 1427119
ノート
印刷プレビュー

反応式

HRID 1427119 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-2e231994c4034df9a744b4d696988668
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933098B2

反応ノート

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