Tetrabutylammonium Fluoride → HCID 44818263, compound

HRID 1158509Notes

Reaction equation

HRID 1158509 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:19]([C@:26]([OH:63])([CH2:43][CH2:44][O:45][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[C:27]([N:29]1[C@H:33]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=3[CH2:40][C@H:32]2[O:31][C:30]1([CH3:42])[CH3:41])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([C@:26]([OH:63])([CH2:43][CH2:44][OH:45])[C:27]([N:29]1[C@H:33]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=3[CH2:40][C@H:32]2[O:31][C:30]1([CH3:42])[CH3:41])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59511564HCID 59511564, compound

Product 1

HCID 44818263HCID 44818263, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.278 g, 1.06 mmol, 1M in THF) was added to a solution of (S)-2-benzyl-4-(tert-butyl-diphenyl-silanyloxy)-1-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3 aH-indeno[1,2-d]oxazol-3-yl)-2-hydroxy-butan-1-one (21f) (0.33 g, 0.53 mmol) in THF (20 mL) at room temperature and stirred for 3 h. Solvent was evaporated and the residue dissolved in dichloromethane and washed with water, brine, dried and evaporated. The product purified by flash chromatography using petroleum ether:acetone (4:1) to get 0.145 g of the title product in 69% yield from two steps.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water, brine
  4. customdried
  5. customevaporated
  6. customThe product purified by flash chromatography

Sources & evidence

ORD record
ord-402da9ecf785410a9f64ccf30e2996cb
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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