Tert-butyl 3-oxopiperidine-1-carboxylate → Tert-butyl 3-[1-(3-fluorophenyl)methylidene]piperidine-1-carboxylate

HRID 928080노트

반응식

HRID 928080 반응식
[Br-].[F:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+].O=[C:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:37]1>C1COCC1.O>[F:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:40]2[CH2:41][CH2:36][CH2:37][N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:39]2)[CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 3

HCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 10527583Phosphonium, [(3-fluorophenyl)methyl]triphenyl-, bromide2회HCID 23676156Sodium t-butoxide

생성물 1

HCID 86713375Tert-butyl 3-[1-(3-fluorophenyl)methylidene]piperidine-1-carboxylate수율 48.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

(3-Fluorobenzyltriphenylphosphonium bromide (Intermediate 228, 5.3 g) was added in portions to a solution of sodium tert-butoxide (1.06 g) in anhydrous THF (20 mL) at room temperature and the mixture was stirred for 30 minutes. A solution of tert-butyl 3-oxopiperidine-1-carboxylate (2 g) in anhydrous THF (10 mL) was added dropwise at room temperature and the mixture was stirred for 24 hours. The mixture was diluted with water (100 mL) and extracted with ether (100 mL), washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexxane with a gradient of 0-20% to give tert-butyl 3-[1-(3-fluorophenyl)-methylidene]piperidine-1-carboxylate (1.42 g).

후처리

  1. stirringthe mixture was stirred for 24 hours
  2. extractionextracted with ether (100 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexxane with a gradient of 0-20%

출처 및 근거

ORD 기록
ord-9b94551b56014567851787861eadf205
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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