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

HRID 719639노트

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HRID 719639 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e6564fcce9604abd80a7b0be0ef1357e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132457B2

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