Tetrabutylammonium Fluoride → 1-(5-Hydroxy-cyclooctyl)-4-hydroxymethyl-3,3-dimethyl-pyrrolidin-2-one

HRID 16218Notes

Reaction equation

HRID 16218 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([SiH2][O:24][C:25](C1C=CC=CC=1)(C1C=CC=CC=1)[CH:26]1[CH2:30][N:29]([CH:31]2[CH2:38][CH2:37][CH2:36][CH:35]([OH:39])[CH2:34][CH2:33][CH2:32]2)[C:28](=[O:40])[C:27]1([CH3:42])[CH3:41])(C)(C)C>O1CCCC1>[OH:39][CH:35]1[CH2:34][CH2:33][CH2:32][CH:31]([N:29]2[CH2:30][CH:26]([CH2:25][OH:24])[C:27]([CH3:41])([CH3:42])[C:28]2=[O:40])[CH2:38][CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131727099HCID 131727099, compound

Product 1

HCID 666652751-(5-Hydroxy-cyclooctyl)-4-hydroxymethyl-3,3-dimethyl-pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutyl ammonium fluoride (0.76 mL, 1 M in tetrahydrofuran, 0.76 mmol) was added to a stirred solution of the product of Example 5J (0.30 g, 0.60 mmol) in tetrahydrofuran (5 mL) at room temperature. The resulting solution was stirred for two hours and then partitioned with ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 20-100% ethyl acetate in hexanes to give the titled product as a white solid.

Workup

  1. custompartitioned with ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified over silica gel using 20-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8012f60afd3942c4875f0b33cff45857
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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