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4-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester → Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate

HRID 238284
ノート
印刷プレビュー

反応式

HRID 238284 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](OC)=[O:27])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1.C(OCC)C>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][OH:27])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 111629634-(2-Methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 21226445Aluminium lithium hydride

生成物 1

HCID 57774474Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate収率 63.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Lithium aluminium hydride (0.026 g, 0.7 mmol) was suspended in dry THF (1 mL) under a nitrogen atmosphere and cooled in an ice bath. A solution of 4-(2-methoxycarbonyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.27 g, 0.7 mmol) in dry THF (2 mL) was added drop wise and the reaction mixture stirred for 1 hour. The reaction mixture was diluted with diethyl ether (5 mL) and quenched with hydrochloric acid (1 N, 5 mL). The organic solution was separated and washed with saturated aqueous sodium hydrogen carbonate (5 mL) and brine (5 mL), dried over magnesium sulphate, filtered and the solvent removed under vacuum to give the title compound as a colourless gum (0.13 g). LCMS m/z 292.0 [M+H]+. R.T.=4.57 min (Analytical Method 4).

後処理

  1. temperaturecooled in an ice bath
  2. customquenched with hydrochloric acid (1 N, 5 mL)
  3. customThe organic solution was separated
  4. washwashed with saturated aqueous sodium hydrogen carbonate (5 mL) and brine (5 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-50c532e69923486da2c92a5aafb588e6
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642621B2

反応ノート

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