Tetrabutylammonium Fluoride → HCID 68526535, compound

HRID 2246737Notes

Reaction equation

HRID 2246737 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH:11]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH3:28])([CH3:27])[C:19]1=[O:29])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][CH:11]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH3:27])([CH3:28])[C:19]1=[O:29])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68528808HCID 68528808, compound

Product 1

HCID 68526535HCID 68526535, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylpropyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (4.0 g, 9.8 mmol) was dissolved in tetrahydrofuran (50 mL) and tetrabutyl ammonium fluoride (1.0 M in THF, 14.7 mL, 14.7 mmol) was added and the mixture was stirred for 1 hour. Reaction was quenched with saturated aqueous ammonium chloride then saturated sodium bicarbonate was added, diluted with ether, washed with water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 10-60% ethyl acetate in hexane) to afford 2.6 g (90%) racemic 1-[3-hydroxy-1-phenylpropyl]-3,3-dimethyl-1,3-dihydro-2H-indol-2-one that was resolved by chiral HPLC.

Workup

  1. customReaction
  2. customwas quenched with saturated aqueous ammonium chloride
  3. additionsaturated sodium bicarbonate was added
  4. additiondiluted with ether
  5. washwashed with water, and saturated brine
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 10-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7d159cd9f0404811b980bba7fdc8fbd6
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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