Dimethylformamide → N-tert-Butyl-3-formyl-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamide
Reaction equation
[C:1]([NH:5][C:6]([C:8]1[S:12][C:11]2[CH2:13][C:14]([CH3:17])([CH3:16])[CH2:15][C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CN([CH:26]=[O:27])C>C1COCC1>[C:1]([NH:5][C:6]([C:8]1[S:12][C:11]2[CH2:13][C:14]([CH3:17])([CH3:16])[CH2:15][C:10]=2[C:9]=1[CH:26]=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 131e (1.5 g, 6.0 mmol) in anhydrous THF (60 mL) cooled to −70° C. was added the solution of n-butyllithium (10.0 mL, 25 mmol, 2.5 Min hexane) over a period of five minutes. See FIG. 15. It was stirred at −70° C. for 6 h. DMF (1.3 g, 18.0 mmol) was added over a period of five minutes and the result mixture was stirred at room temperature overnight. It was then quenched with saturated NH4Cl (40 mL) and concentrated under reduced pressure. The residue was extracted with ethyl acetate (2×30 mL). The combined organic layer was dried over anhydrous Mg2SO4 and filtered. The filtrate was evaporated under reduced pressure to afford 131f as a yellow solid (1.34 g, 80%). MS-ESI: [M+H]+ 280.3
Workup
- stirringthe result mixture was stirred at room temperature overnight
- customIt was then quenched with saturated NH4Cl (40 mL)
- concentrationconcentrated under reduced pressure
- extractionThe residue was extracted with ethyl acetate (2×30 mL)
- dry with materialThe combined organic layer was dried over anhydrous Mg2SO4
- filtrationfiltered
- customThe filtrate was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-d4cd2578cbe24fe6811b07d7fd8ba20b
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946213B2
Reaction notes
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