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

HRID 862190노트

반응식

HRID 862190 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 8 h. 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 6.7 g of a white solid.

후처리

  1. temperaturethe biphasic solution was heated to reflux
  2. temperatureThe reaction was heated for 8 h.
  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-2021657eb85f450a97a793f837ae6338
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05717100

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