Allyl Alcohol → 2-Chloro-5(3-oxopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide
Reaction equation
[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]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
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).
Workup
- customto afford a pale brown mixture which
- temperatureThe resulting dark brown mixture was cooled
- filtrationto ambient then filtered
- customto remove the solid residues
- washThese were washed with further toluene (2×50 ml)
- washthe combined toluene extracts then washed with water (100 ml)
- dry with materialdried over MgSO4
- concentrationconcentrated to a light brown solid (3.82 g)
Sources & evidence
- ORD record
- ord-aff71262104e47759891e5a9f0e46db0
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07297818B2
Reaction notes
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