Lithium Hydroxide → N-Boc-4-cyanopiperidine-4-carboxylic acid

HRID 423062

반응식

HRID 423062 반응식
[OH-].[Li+].[C:3]([C:5]1([C:18]([O:20]CC)=[O:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)#[N:4]>C1COCC1.C(OCC)C>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([C:3]#[N:4])([C:18]([OH:20])=[O:19])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 577503761-tert-Butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate2회

생성물 1

HCID 57750275N-Boc-4-cyanopiperidine-4-carboxylic acid수율 91%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

An aqueous solution of lithium hydroxide (2M, 39.0 mL, 77.92 mmol) was added to a stirred solution of 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate (Intermediate 7) (5.5 g, 19.48 mmol), in THF (78 mL) at 25° C. The resulting mixture was stirred at 25° C. for 3 hours and monitored by TLC. The reaction mixture was diluted with diethyl ether (150 mL), and washed with water (100 mL). The aqueous layers were combined and then acidified with citric acid (1N, 200 mL). The product was extracted into DCM. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford 1-(tert-butoxycarbonyl)-4-cyanopiperidine-4-carboxylic acid (4.50 g, 91%). This material was used in the next steps without further purification.

후처리

  1. washwashed with water (100 mL)
  2. extractionThe product was extracted into DCM
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-913c783346914bb1a7ddaff84e3acc07
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101623B2

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