Tetrabutylammonium Fluoride → HCID 70976202, compound
Reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][C@@H:7]1[CH2:27][N:10]2[C:11](=[O:26])[N:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:16][CH:15]=3)[CH2:13][C@H:9]2[CH2:8]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][C@@H:7]1[CH2:27][N:10]2[C:11](=[O:26])[N:12]([C:14]3[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])=[CH:18][CH:19]=3)[CH2:13][C@H:9]2[CH2:8]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (6S,7aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-hexahydro-pyrrolo[1,2-c]imidazol-3-one (250 mg, 0.451 mmol) in THF (3 mL) was added TBAF (1M in THF, 0.55 ml, 0.541 mmol) at 0° C. and stirred for 4 h at room temperature. The mixture was concentrated under reduced pressure and the residue was taken up with DCM. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified through column chromatography over silica (elution with 20% ethyl acetate in hexane) to afford 130 mg (90%) of the title compound. LC-MS: 317.4 [M+1]+.