Tetrabutylammonium Fluoride → 9-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

HRID 2115619Notes

Reaction equation

HRID 2115619 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]([CH:23]1[CH2:30][CH:29]2[CH:31]([N:32]3[CH2:36][CH:35]([C:37](C4C=CC=CC=4)(C4C=CC=CC=4)[O:38][SiH2]C(C)(C)C)[C:34]([CH3:57])([CH3:56])[C:33]3=[O:58])[CH:25]([CH2:26][CH2:27][CH2:28]2)[CH2:24]1)=[O:22]>O1CCCC1>[CH3:19][O:20][C:21]([CH:23]1[CH2:30][CH:29]2[CH:31]([N:32]3[CH2:36][CH:35]([CH2:37][OH:38])[C:34]([CH3:56])([CH3:57])[C:33]3=[O:58])[CH:25]([CH2:26][CH2:27][CH2:28]2)[CH2:24]1)=[O:22]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317271009-[4-(Tert-butyl-diphenyl-silanyloxymethyl)-3,3-dimethyl-2-oxo-pyrrolidin-1-yl]-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Product 1

HCID 666569529-(4-Hydroxymethyl-3,3-dimethyl-2-oxo-pyrrolidin-1-yl)-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutyl ammonium fluoride (3.2 mL, 1 M in tetrahydrofuran, 3.2 mmol) was added to a stirred solution of Example 7C (0.9 g, 1.56 mmol) in tetrahydrofuran 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 title 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-4d7c22bbdb6b4fb891a09953c351742f
Source dataset
uspto-grants-2008_10
Patent number
US07435833B2

Reaction notes

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