Tetrabutylammonium Fluoride → [2-(2-Hydroxyethoxy)ethoxy]methylcarbamic acid tert-butyl ester

HRID 2093242Notes

Reaction equation

HRID 2093242 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][N:31]([CH3:39])[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])(C)(C)C>C1COCC1>[CH3:39][N:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[O:30][CH2:29][CH2:28][O:27][CH2:26][CH2:25][OH:24]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86643773O-{2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethoxy]-ethyl}-N-methyl-N-BOC-hydroxylamine

Product 1

HCID 86643775[2-(2-Hydroxyethoxy)ethoxy]methylcarbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (6.78 mL, 6.78 mmol) was added to O-{2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethoxy]-ethyl}-N-methyl-N-BOC-hydroxylamine (d) (3 g, 6.33 mmol) dissolved in dry THF (15 mL). The reaction was stirred over night. The THF was evaporated off and the residue was dissolved in DCM and washed with NH4Cl (saturated) (40 mL), water and brine. The organic phase was dried (MgSO4) and evaporated off. The residue was purified using flash chromatography on a Companion Combiflash 40 g column (Gradient MeOH 0-5% over 20 minutes in DCM. Structure confirmed by NMR.

Workup

  1. customThe THF was evaporated off
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with NH4Cl (saturated) (40 mL), water and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated off
  6. customThe residue was purified
  7. customover 20 minutes

Sources & evidence

ORD record
ord-65ceeeb5788c4d60a7f0d86a84da181c
Source dataset
uspto-grants-2013_05
Patent number
US08444955B2

Reaction notes

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