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

HRID 1184990ノート

反応式

HRID 1184990 の反応式
[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

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 69763Di-p-tolylcarbodiimideHCID 137994TempolHCID 178418361HCID 178418361、化合物2 回

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4fe92e9146c04b1e88aafceca9fb7863
出典データセット
uspto-grants-2014_03
特許番号
US08669398B2

反応ノート

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