Tetrabutylammonium Fluoride → HCID 44819176, compound

HRID 1158532Notes

Reaction equation

HRID 1158532 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 68676989HCID 68676989, compound

Product 1

HCID 44819176HCID 44819176, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (0.274 g, 1.05 mmol, 1M in THF) was added to a solution of (R)-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 (46) (0.325 g, 0.52 mmol) in THF (20 mL) at room temperature and stirred for 3 h. The solvent was evaporated and the residue dissolved in dichloromethane and washed with water and brine, dried and evaporated. The product was purified by flash chromatography using petroleum ether:acetone (4:1) which gave 0.140 g of the title compound in 53% yield from two steps.

Workup

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

Sources & evidence

ORD record
ord-2d9d0a1f147f465a98e3a73d2ae4e376
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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