Tetrabutylammonium Fluoride → HCID 67061919, compound

HRID 337574Notes

Reaction equation

HRID 337574 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][O:24][Si](C(C)(C)C)(C)C)[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH2:23][OH:24])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66899583HCID 66899583, compound

Product 1

HCID 67061919HCID 67061919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl cyclopropyl{[6-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-8-quinolinyl]methyl}carbamate (1 eq.) from the previous step in THF (0.12 M) was added TBAF (1.0 M in hexane, 1.6 eq.). The resulting solution was stirred at RT for 2 h before the volatiles were removed in vacuo. The resulting residue was partitioned between ether and water. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customwere removed in vacuo
  2. customThe resulting residue was partitioned between ether and water
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-fea1743e0534436a8f525987ddd86e46
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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