Acetic Acid → N-Ethylcarbamate 4-chloro-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole
Reaction equation
[Cl:1]N1C(=O)CCC1=O.C(O)(=O)C.[CH2:13]([NH:15][C:16](=[O:18])[O-:17])[CH3:14].[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[CH:25]([CH3:33])[CH:26]3[CH2:30][NH:29][CH2:28][CH:27]3[C:31]=2[CH:32]=1>ClCCCl.C(Cl)Cl>[CH2:13]([NH:15][C:16](=[O:17])[O-:18])[CH3:14].[Cl:1][C:32]1[C:31]2[CH:27]3[CH2:28][NH:29][CH2:30][CH:26]3[CH:25]([CH3:33])[C:24]=2[CH:23]=[CH:22][C:21]=1[O:20][CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
N-chlorosuccinimide (0.39 g, 2.9 mmol) and acetic acid (3 mL) were added to a solution of N-ethylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, Step A) (0.80 g, 2.9 mmol) in DCE (3 mL). The resulting solution was stirred for 3 hours at 60° C. The reaction mixture was cooled to room temperature, diluted with CH2Cl2 (50 mL), and washed with H2O (50 mL). The organic extract was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (SiO2) using a 0-35% EtOAc-hexanes gradient to afford 50 mg (6%) of the subtitle compound (The major product is N-ethylcarbamate-5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole, 78%). MS calculated for C16H20ClNO3+H: 310, observed: 310.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- washwashed with H2O (50 mL)
- extractionThe organic extract
- dry with materialwas dried over MgSO4
- concentrationconcentrated
- customThe crude product was purified by column chromatography (SiO2)
Sources & evidence
- ORD record
- ord-4b8094396c6d4a6f98defb2e001999aa
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935830B2
Reaction notes
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