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

HRID 2287420노트

반응식

HRID 2287420 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-67bce80067e049fca4dcee52af935610
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06083949

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