Acetic Acid → 4-Benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

HRID 2287420ノート

反応式

HRID 2287420 の反応式
C([O:3][C:4]([C:6]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].C(O)(=O)C>C(O)(C)C.C1COCC1.O>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

参加物

7

反応物 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 162182711-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate

生成物 1

HCID 121510204-Benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid収率 66.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirring solution of 4-benzylpiperidine-1,4-dicarboxylic acid tert-butyl ester ethyl ester (31.6 mmol, 11.01 g) in isopropyl alcohol (50 mL) and THF (50 mL) was added 3N NaOH (63.4 mmol, 21.1 mL) and the biphasic solution was heated to reflux. The reaction was heated for 8h. and then left stirring at room temperature overnight. The reaction was then diluted with water (200 mL) and acidified to pH=4 with glacial acetic acid. The aqueous mixture was then extracted with ethyl acetate (2×500 mL). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The resulting solid was triturated with diethyl ether to give 6.7g of a white solid.

後処理

  1. temperaturethe biphasic solution was heated to reflux
  2. temperatureThe reaction was heated for 8h.
  3. waitleft
  4. extractionThe aqueous mixture was then extracted with ethyl acetate (2×500 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting solid was triturated with diethyl ether

出典と根拠

ORDレコード
ord-67bce80067e049fca4dcee52af935610
出典データセット
uspto-grants-2000_07
特許番号
US06083949

反応ノート

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