Tetrabutylammonium borohydride → HCID 67070116, compound
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)=O.[BH4-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[F:1][C:2]([F:16])([F:17])[CH2:3][NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
step c—A vial was charged with 122 (1.0 g, 4.05 mmol) and DCM (15 mL) then tetrabutylammonium borohydride was added. The vial was capped and heated overnight in an oil bath at 50° C. The reaction mixture was cooled to RT and the DCM was evaporated. HOAc was added dropwise until H2 evolution ceased. The solvents were evaporated and toluene was added. The mixture was made basic with dilute NaHCO3, extracted with EtOAc, dried (MgSO4), filtered and evaporated. The resulting solid was recrystallized from hexane to afford 0.349 g of methyl 4-(2,2,2-trifluoro-ethylamino)-benzoate (124)