Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.O[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([C:39]2[CH:48]=[CH:47][CH:46]=[CH:45][C:40]=2[C:41]([O:43][CH3:44])=[O:42])[CH2:34]1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1.O>[CH3:44][O:43][C:41]([C:40]1[CH:45]=[CH:46][CH:47]=[CH:48][C:39]=1[N:35]1[CH2:36][CH2:37][CH2:38][CH:33]([CH2:32][N:24]2[C:20](=[O:30])[C:21]3=[CH:29][CH:28]=[CH:27][CH:26]=[C:22]3[C:23]2=[O:25])[CH2:34]1)=[O:42]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Triphenylphosphine (1.68 g, 6.20 mmol) and phthalimide (799 mg, 5.43 mmol) were added to methyl 2-[3-(hydroxymethyl)piperidin-1-yl]benzoate (1.29 g, 5.17 mmol) in tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 10 min and a 40% diethyl azodicarboxylate/toluene solution (3.52 mL, 7.76 mmol) was added. The mixture was then stirred at room temperature for 8 hours. Subsequently, water was added and the mixture was extracted with ethylacetate. The extract was washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 1.85 g (95%) of the desired compound as a pale yellow oil.
Workup
- stirringThe mixture was then stirred at room temperature for 8 hours
- extractionthe mixture was extracted with ethylacetate
- washThe extract was washed with brine
- dry with materialby drying over magnesium sulfate and evaporation of the solvent
- customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)
Sources & evidence
- ORD record
- ord-0cc93c605ff844d78e7a84d99a0d7f4f
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902367B2
Linked notes
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