Tetrabutylammonium Fluoride → HCID 67973570, compound

HRID 1184732Notes

Reaction equation

HRID 1184732 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH:32]2[CH2:36][C:35]3[CH:37]=[C:38]([C:41]4[O:45][C:44]([Si](C(C)C)(C(C)C)C(C)C)=[N:43][CH:42]=4)[CH:39]=[CH:40][C:34]=3[O:33]2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH:32]2[CH2:36][C:35]3[CH:37]=[C:38]([C:41]4[O:45][CH:44]=[N:43][CH:42]=4)[CH:39]=[CH:40][C:34]=3[O:33]2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67973864HCID 67973864, compound

Product 1

HCID 67973570HCID 67973570, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride solution (1 M in tetrahydrofuran; 1.00 mL) is added to an ice cooled solution of 4-[5-(2-triisopropylsilanyl-oxazol-5-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (190 mg) in tetrahydrofuran (5 mL) and the resulting mixture is stirred for 1 h. The ice bath is removed and the reaction mixture is stirred for an additional hour at room temperature. Ethyl acetate and water are added; the organic phase is separated, dried over MgSO4, and concentrated in vacuo. The residue is recrystallised from diisopropylether. LC (method 6): tR=1.32 min; Mass spectrum (ESI+): m/z=371 [M+H]+.

Workup

  1. customThe ice bath is removed
  2. stirringthe reaction mixture is stirred for an additional hour at room temperature
  3. additionEthyl acetate and water are added
  4. customthe organic phase is separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is recrystallised from diisopropylether

Sources & evidence

ORD record
ord-af6897f5e42b455284640e09bde0f033
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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