Water → 4-[2-(4-Fluorophenyl)ethylidene]-piperidine-1-carboxylic acid benzyl ester

HRID 12370

반응식

HRID 12370 반응식
[Br-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.O=[C:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[CH2:33][CH2:32]1.O>C1COCC1>[CH2:40]([O:39][C:37]([N:34]1[CH2:35][CH2:36][C:31](=[CH:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=2)[CH2:32][CH2:33]1)=[O:38])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 223867454-Fluorophenethyltriphenylphosphonium bromide

생성물 1

HCID 574260424-[2-(4-Fluorophenyl)ethylidene]-piperidine-1-carboxylic acid benzyl ester수율 17.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of phosphonium bromide 78NLS66 (4.69 g, 10.1 mmol) in THF (100 mL) n-butyllithium (1.6 M in hexane, 6.3 mL, 10.1 mmol) was added at 0° C., giving a deep red solution. After stirring for 1 h at rt, a solution of benzyl 4-oxo-1-piperidinecarboxylate (2.24 g, 9.6 mmol) in THF (10 mL) was added dropwise over 30 min. The mixture was stirred at rt for 20 h, then water was added and the mixture extracted three times with diethylether. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue by silica gel column chromatography, eluting with a stepwise gradient of 0-10% ethyl acetate in n-heptane, afforded the title compound (0.56 g, 17%) as a colourless oil.

후처리

  1. additionwas added at 0° C.
  2. customgiving a deep red solution
  3. stirringThe mixture was stirred at rt for 20 h
  4. extractionthe mixture extracted three times with diethylether
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by silica gel column chromatography
  9. washeluting with a stepwise gradient of 0-10% ethyl acetate in n-heptane

출처 및 근거

ORD 기록
ord-82c7cda0ea19489b8bb5ea8f54195000
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727999B2

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