Tetrabutylammonium Fluoride → HCID 86622950, compound

HRID 1715396Notes

Reaction equation

HRID 1715396 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:47])[N:25]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38](C)(C)[O:39][SiH2]C(C)(C)C)[CH:32]=1)[CH2:26][CH:27]([F:29])[F:28])([CH3:22])([CH3:21])[CH3:20]>C1COCC1.CCOC(C)=O>[C:19]([O:23][C:24](=[O:47])[N:25]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][OH:39])[CH:32]=1)[CH2:26][CH:27]([F:29])[F:28])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131728333HCID 131728333, compound

Product 1

HCID 86622950HCID 86622950, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBAF (1M in THF, 9.57 mL, 9.57 mmol) was added dropwise to a sol. of [3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (2.15 g, 4.78 mmol) in THF (48 mL) at 0° C. The mixture was was stirred for 1 h while warming up to rt. The mixture was diluted with EtOAc, and the resulting mixture was washed with aq. sat. NH4Cl (2×) and brine (1×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 30:70) yielded the title compound (591 mg, 37%). LC-MS: tR=0.97 min; ES+: 336.09.

Workup

  1. washthe resulting mixture was washed with aq. sat. NH4Cl (2×) and brine (1×)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (EtOAc/heptane 30:70)

Sources & evidence

ORD record
ord-012ac4ace5cf41aaac0bb5a14ef3dd4e
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

Loading…