Tetrabutylammonium Fluoride → HCID 178501185, compound

HRID 518602Notes

Reaction equation

HRID 518602 reaction equation
[F:1][C:2]1[CH:41]=[CH:40][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:27]=[CH:26][C:25]([CH2:28][O:29][Si](C(C)C)(C(C)C)C(C)C)=[CH:24][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178501186HCID 178501186, compound

Product 1

HCID 178501185HCID 178501185, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

cis-Methyl 4-((E)-2-(4-fluorobenzoylimino)-6-((triisopropylsilyloxy)methyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylate (0.61 g, 1.048 mmol) was suspended in 2.1 mL of THF and cooled to 0° C. under nitrogen. To this mixture was added TBAF (1 M in THF) (1.573 mL, 1.573 mmol) dropwise via syringe, and the resulting mixture was stirred for 30 minutes at 0° C. The ice bath was removed, and the mixture was stirred for another 30 minutes at RT. The resulting mixture was diluted with DCM and washed with water. The organic layer was collected, dried over sodium sulfate, and concentrated, and the residue was purified by silica gel chromatography (30-50% EtOAc/Hexanes) to provide the title compound (190 mg, 42.6% yield). MS m/z=426.2 [M+H]. Calc'd for C23H24FN3O4: 425.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.63-1.92 (m, 4H) 2.15-2.30 (m, 2H) 2.53-2.74 (m, 2H) 2.78-2.94 (m, 1H) 3.76 (s, 3H) 4.58 (d, J=5.58 Hz, 2H) 4.62-4.82 (m, 1H) 5.24 (t, J=5.58 Hz, 1H) 7.11-7.20 (m, 1H) 7.20-7.33 (m, 2H) 7.35-7.66 (m, 2H) 7.84-8.46 (m, 2H) 12.78 (s, 1H).

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred for another 30 minutes at RT
  3. additionThe resulting mixture was diluted with DCM
  4. washwashed with water
  5. customThe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel chromatography (30-50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-addbe9dc892847f0afaba13c203d00d2
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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