Hydrochloric Acid → Lauryl 3-[N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-hydroxyamino]propionate

HRID 741783

反応式

HRID 741783 の反応式
[CH2:1]([O:9][N:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][C:13](=[N:18][OH:19])[CH2:12][C:11]1([CH3:21])[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[H][H].[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])(=[O:28])[CH:26]=[CH2:27]>[Pt].CO>[CH2:1]([O:9][N:10]1[C:11]([CH3:20])([CH3:21])[CH2:12][CH:13]([N:18]([CH2:27][CH2:26][C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])[OH:19])[CH2:14][C:15]1([CH3:17])[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 75084Lauryl acrylateHCID 229026981-Octyloxy-2,2,6,6-tetramethylpiperidin-4-one oximeHCID 178418361HCID 178418361、化合物

生成物 1

HCID 22902716Lauryl 3-[N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-hydroxyamino]propionate収率 57.8%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 887Methanol溶媒

実験手順

A mixture of 1-octyloxy-2,2,6,6-tetramethylpiperidin-4-one oxime (10.0 g, 35.4 mmol) (a mixture of octyloxy isomers) 5.5 ml of concentrated hydrochloric acid and 130 ml of methanol is subjected to 3 atmospheres of hydrogen over 5% platinum on carbon for 18 hours. The reaction mixture is filtered through celite and then concentrated. The residue is partitioned between ethyl acetate and aqueous potassium carbonate. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate and finally concentrated to a total volume of about 150 ml. Lauryl acrylate (7.7 g, 32 mmol ) is added. After a two-hour reaction time, the reaction mixture is concentrated and the crude product purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate) to yield 10.0 g (52% yield) of a clear oil.

後処理

  1. filtrationThe reaction mixture is filtered through celite
  2. concentrationconcentrated
  3. customThe residue is partitioned between ethyl acetate and aqueous potassium carbonate
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfinally concentrated to a total volume of about 150 ml
  7. customAfter a two-hour reaction time
  8. concentrationthe reaction mixture is concentrated
  9. customthe crude product purified by flash chromatography on silica gel (9:1, hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-6edf92e84dbe4363b2dee818ac08c813
出典データセット
uspto-grants-1996_09
特許番号
US05552464

関連ノート

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