Tetrahydrofuran → 2-(4-Hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-1,3-di-p-tolyl-isourea

HRID 1184990노트

반응식

HRID 1184990 반응식
[CH3:1][C:2]1([CH3:12])[N:7]([O])[C:6]([CH3:10])([CH3:9])[CH2:5][CH:4]([OH:11])[CH2:3]1.[H][H].[C:15]1([CH3:31])[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[N:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[CH:17][CH:16]=1.C1C[O:35]CC1>>[OH:11][CH:4]1[CH2:3][C:2]([CH3:12])([CH3:1])[N:7]([O:35][C:22](=[N:23][C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)[NH:21][C:18]2[CH:19]=[CH:20][C:15]([CH3:31])=[CH:16][CH:17]=2)[C:6]([CH3:10])([CH3:9])[CH2:5]1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 69763Di-p-tolylcarbodiimideHCID 137994TempolHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 585261802-(4-Hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-1,3-di-p-tolyl-isourea

실험 절차

4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (1.9 g, 11 mmol) is dissolved in THF (40 ml) and hydrogenated in the presence of 0.035 g Pt (5% on carbon) catalyst using 4 bar hydrogen pressure. The hydrogen uptake stops after approximately one hour. The reaction mixture is then filtered and mixed with the solution of bis-p-tolyl-carbodiimide (2.45 g, 11 mmol) in THF (30 ml). The solution is stirred under argon at room temperature for 16 hours and concentrated. The residue is chromatographed on silica gel with hexane-ethyl acetate (1:1) and the pure fractions are crystallized from ethyl acetate to afford 1.6 g of the title compound as a colorless solid, mp. 124-126° C.

후처리

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated
  3. customThe residue is chromatographed on silica gel with hexane-ethyl acetate (1:1)
  4. customthe pure fractions are crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-4fe92e9146c04b1e88aafceca9fb7863
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669398B2

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