Dimethylformamide → tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate
Reaction equation
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C#C.CC[N:19](CC)[CH2:20][CH3:21].C[N:25](C=O)C>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:25]1[CH:21]=[CH:20][N:19]=[C:1]1[C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 4 (0.78 g, 1.7 mmol), acetylene intermediate A5 (0.56 g, 1.7 mmol, synthesized as described in Scheme 1-1), CuI (63 mg, 0.33 mmol), and Et3N (0.67 mL, 5.0 mmol) in DMF (20 mL) was added Pd(PPh3)4 (0.19 g, 0.165 mmol). The resulting mixture was degassed with N2, and then stirred at 100° C. overnight in a sealed tube. The reaction mixture was slowly dropped into H2O (100 mL). The precipitate was collected and then dissolved in EtOAc. The organic phase was dried, filtered, and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (EtOAc) to afford 5 (420 mg, 34% yield). LC-MS (ESI): m/z 746.4 (M+H)+
Workup
- customThe resulting mixture was degassed with N2
- additionThe reaction mixture was slowly dropped into H2O (100 mL)
- customThe precipitate was collected
- dissolutiondissolved in EtOAc
- customThe organic phase was dried
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a residue, which
- customwas purified by silica gel column chromatography (EtOAc)
Sources & evidence
- ORD record
- ord-a3a82204f86140158d54f4c1312aaad7
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865756B2
Reaction notes
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