Tetrabutylammonium Fluoride → HCID 66912359, compound

HRID 1830946Notes

Reaction equation

HRID 1830946 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C:21]1[C:26]2[C:27](=[O:52])[N:28]3[CH2:43][C@H:42]([O:44][Si](C(C)(C)C)(C)C)[CH2:41][C@H:29]3[C:30](=[O:40])[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:25]=2[CH:24]=[CH:23][C:22]=1[O:53][CH3:54]>C1COCC1.C(Cl)Cl>[CH3:19][O:20][C:21]1[C:26]2[C:27](=[O:52])[N:28]3[CH2:43][C@H:42]([OH:44])[CH2:41][C@H:29]3[C:30](=[O:40])[N:31]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:37])[CH3:38])[C:25]=2[CH:24]=[CH:23][C:22]=1[O:53][CH3:54]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23574468HCID 23574468, compound

Product 1

HCID 66912359HCID 66912359, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1 N TBAF in THF (19.58 mL, 19.58 mmol) was added to a stirred solution of 172 (7.0 g, 13.05 mmol) in THF (50 mL). The reaction mixture was allowed to stir at room temperature for 2 hours and diluted with DCM (200 mL), washed with water (2×200 mL), brine (2×200 mL) and dried over anhydrous MgSO4. Filtration and removal of excess solvent afforded the crude product, which was purified by flash column chromatography using 50:50 petroleum ether:EtOAc as eluent. Evaporation in vacuo of the pure fractions afforded the product (173) (5.9 g). 1H NMR (270 MHz, CDCl3) δ7.30 (s, 1H, ArH), 7.24 (s, 1H, ArH), 5.52 (d, 1H, J=9.9 Hz, SEM amino acetal CH2), 4.68-4.64 (m, 2H, SEM amino acetal CH2+2), 4.30 (dd, 1H, J=5.86, 8.24 Hz), 3.91 (s, 3H, OMe), 3.90 (s, 3H, OMe), 3.87-3.51 (m, 4H, SEM 1′ CH2+3), 2.95 (dt, 1H, J=5.31, 13.56 Hz, 1), 2.17-2.08 (m, 1H, 1), 1.02-0.93 (m, 2H, SEM 2′ CH2), 0.03 (s, 9H, 3× SiCH3); 13C NMR (67.8 MHz, CDCl3) δ169.7, 165.9, 151.9, 147.1, 134.0, 121.1, 111.2, 105.5, 78.2, 69.1, 67.1, 56.5, 56.1, 53.9, 34.9, 18.4, −1.3.

Workup

  1. washwashed with water (2×200 mL), brine (2×200 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationFiltration and removal of excess solvent
  4. customafforded the crude product, which
  5. customwas purified by flash column chromatography
  6. customEvaporation in vacuo of the pure fractions

Sources & evidence

ORD record
ord-40ab9ca3d2a64b7e98aadb9d6f4e6642
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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