HCID 117966280, compound → HCID 117966443, compound
Reaction equation
[CH2:1]1[N:5]=[C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[N:3]2[CH2:19][CH2:20][CH2:21][CH:2]12>C1(C)C=CC=CC=1>[CH:1]1[N:5]=[C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:7]2)[N:3]2[CH2:19][CH2:20][CH2:21][C:2]=12Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 115 °C
Procedure
To a solution of tert-butyl 3-(5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-3-yl)piperidine-1-carboxylate (175 mg, 0.6 mmol) in toluene (5 mL) was added BaMnO4 (2.1 g, 18 mmol) and the reaction was heated at 115° C. for 42 h. The reaction was cooled to room temperature and BaMnO4 (2 g) was added followed by toluene (2 mL). The reaction mixture was heated to 115° C. for 3 days. The mixture was cooled to room temperature and filtered through Celite followed by rinsing with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified via HPLC to afford tert-butyl 3-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-3-yl)piperidine-1-carboxylate as an oil (25 mg, 14%). MS (ES+) (M+H) 292.2; LCMS retention time: 1.69 minutes (Method M).