2,6-Dimethylphenol → Methyl 4-{[4-(2,6-dimethylphenoxy)piperidin-1-yl]methyl}-3-isopropoxybenzoate

HRID 507989노트

반응식

HRID 507989 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[O:19][CH:20]([CH3:22])[CH3:21])[CH2:4][CH2:3]1.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1O.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.C(OCC)C>[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[O:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[O:19][CH:20]([CH3:22])[CH3:21])[CH2:4][CH2:3]1

참가 물질

7

반응물 4

HCID 113352,6-Dimethylphenol2회HCID 13831Tributylphosphine2회HCID 730421,1'-(Azodicarbonyl)dipiperidine2회HCID 23157343Methyl 4-[(4-hydroxypiperidin-1-yl)methyl]-3-isopropoxybenzoate

생성물 1

HCID 23157284Methyl 4-{[4-(2,6-dimethylphenoxy)piperidin-1-yl]methyl}-3-isopropoxybenzoate수율 36.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-[(4-hydroxypiperidin-1-yl)methyl]-3-isopropoxybenzoate (0.72 g, 2.34 mmol), 2,6-dimethylphenol (0.43 g, 3.51 mmol) and tributylphosphine (0.88 mL, 3.51 mmol) in anhydrous tetrahydrofuran (14 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.89 g, 3.51 mmol), and the mixture was stirred at room temperature for 12 hr. To the reaction mixture were added reagents (2,6-dimethylphenol, tributylphosphine and 1,1′-(azodicarbonyl)dipiperidine) in the same amount as mentioned above, and the mixture was further stirred for 12 hr. Diethyl ether (40 mL) was added to the reaction solution, the precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (0.35 g, yield 36%) as a colorless oil.

후처리

  1. stirringwas further stirred for 12 hr
  2. filtrationthe precipitate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

출처 및 근거

ORD 기록
ord-09029761993d4faa807ebcd5e9a8491f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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