Trifluoroacetic acid → Ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate
Reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][C:4]=2[CH:3]=[C:2]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 100-mL round-bottom flask charged with 5-tert-butyl 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate (1 g, 3.21 mmol; prepared as described in J. Med. Chem. 2006, 49(15):4623-4637) and DCM (16 mL) was slowly added trifluoroacetic acid (1.48 mL, 19.3 mmol) at 0° C. The solution was then stirred at room temperature for 60 min. To the reaction mixture was then added saturated aqueous NaHCO3 solution (10 mL) and DCM (10 mL). Upon separation of the layers, the aqueous solution was further extracted with DCM (20 mL) twice. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated to give ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (0.547 g, 81%) as an oil. LCMS: (FA) ES+ 212.
Workup
- customat 0° C
- customUpon separation of the layers
- extractionthe aqueous solution was further extracted with DCM (20 mL) twice
- washThe combined organic layers were washed with brine
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a5e374ed4a584f458ea45f78ef2db71b
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08624040B2
Reaction notes
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