Water → tert-Butyl 4-(3-(6-methylpyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

HRID 1666391노트

반응식

HRID 1666391 반응식
[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=2)[CH2:12]P(=O)(OCC)OCC)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].O>C1COCC1.O1CCOCCOCCOCCOCC1>[CH3:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=2)[CH:12]=[C:36]2[CH2:37][CH2:38][N:33]([C:31]([O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:32])[CH2:34][CH2:35]2)[CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 86623900Diethyl 3-(6-methylpyridin-2-yloxy)benzylphosphonate

생성물 1

HCID 68950276tert-Butyl 4-(3-(6-methylpyridin-2-yloxy)benzylidene)piperidine-1-carboxylate수율 83%

시약·촉매·용매 2

HCID 3633615-Crown-5촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Diethyl 3-(6-methylpyridin-2-yloxy)benzylphosphonate (4.7 g, 14 mmol) from Step 3 and 1,4,7,10,13-pentaoxacyclopentadecane (15-Crown-5, 0.05 mL, 0.28 mmol) were combined in THF (150 mL). Sodium hydride (617 mg, 60% dispersion in mineral oil, 15.4 mmol) was added. The reaction was stirred for 30 min and then a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (3.07 g, 15.4 mmol) in THF (15 mL) was added. After 16 h, water was added and the layers were separated. The aqueous layer was extracted with EtOAc (2×200 mL) and the combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (10-30%, EtOAc:heptane) to afford the title compound (4.4 g, 83% yield) as a thick oil.

후처리

  1. waitAfter 16 h
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  4. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (10-30%, EtOAc:heptane)

출처 및 근거

ORD 기록
ord-1928fc4e924647e5a2746aec035dcd9b
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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