Tetrabutylammonium Fluoride → HCID 70976202, compound

HRID 455277Notes

Reaction equation

HRID 455277 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]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70975872HCID 70975872, compound

Product 1

HCID 70976202HCID 70976202, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified through column chromatography over silica (elution with 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-94ee03beb9c94167b08e0474d6d003d9
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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