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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
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HRID 238284 반응식
[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]
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50c532e69923486da2c92a5aafb588e6
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642621B2

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