Water → Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylate

HRID 2366479ノート

反応式

HRID 2366479 の反応式
CON(C)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.ClCCl>[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)=[CH:8][CH:7]=1)=[O:5]

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86613864Tert butyl 4-(4-(methoxy(methyl)carbamoyl)phenyl)piperidine-1-carboxylate

生成物 1

HCID 11254770Tert-butyl 4-(4-formylphenyl)piperidine-1-carboxylate収率 27%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of EXAMPLE 88A (0.8 g, 2.3 mmol) in tetrahydrofuran (5 mL) was cooled to −78° C. and treated with lithium aluminum hydride (0.25 g, 6.6 mmol). The mixture was stirred for 30 minutes and treated with water (1 mL) and 15% sodium hydroxide (0.25 mL). Dichloromethane was added and the mixture dried over magnesium sulfate and filtered through silica gel. The solution was concentrated and purified by flash chromatography on silica gel using 1:1 hexane/ethyl acetate to provide the title compound (0.18 g).

後処理

  1. dry with materialthe mixture dried over magnesium sulfate
  2. filtrationfiltered through silica gel
  3. concentrationThe solution was concentrated
  4. custompurified by flash chromatography on silica gel using 1:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-0099c68ad03942ffbe6e7e8c54579c00
出典データセット
uspto-grants-2014_04
特許番号
US08697736B2

反応ノート

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