Allyl Alcohol → 2-Chloro-5(3-oxopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1593821ノート

反応式

HRID 1593821 の反応式
[Cl:1][C:2]1[CH:21]=[CH:20][C:19](I)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].C(=O)([O-])O.[Na+].[CH2:28]([OH:31])[CH:29]=[CH2:30]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:30][CH2:29][CH:28]=[O:31])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

参加物

7

反応物 3

HCID 7858Allyl AlcoholHCID 516892Sodium BicarbonateHCID 120853472-Chloro-5iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

生成物 1

HCID 120853482-Chloro-5(3-oxopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

2-Chloro-5-iodo-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (5.00 g, Example 14a), tetrabutylammonium chloride (3.40 g) and sodium hydrogencarbonate (2.44 g) were charged to a flask. Pd(OAc)2 (0.0533 g), toluene (50 ml) and allyl alcohol (1.01 ml) were added to afford a pale brown mixture which was heated at 80° C. for 5 h. The resulting dark brown mixture was cooled to ambient then filtered to remove the solid residues. These were washed with further toluene (2×50 ml) and the combined toluene extracts then washed with water (100 ml), dried over MgSO4 and concentrated to a light brown solid (3.82 g).

後処理

  1. customto afford a pale brown mixture which
  2. temperatureThe resulting dark brown mixture was cooled
  3. filtrationto ambient then filtered
  4. customto remove the solid residues
  5. washThese were washed with further toluene (2×50 ml)
  6. washthe combined toluene extracts then washed with water (100 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to a light brown solid (3.82 g)

出典と根拠

ORDレコード
ord-aff71262104e47759891e5a9f0e46db0
出典データセット
uspto-grants-2007_11
特許番号
US07297818B2

反応ノート

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