Tetrabutylammonium Fluoride → HCID 131729315, compound

HRID 657152Notes

Reaction equation

HRID 657152 reaction equation
CC([Si](C)(C)[O:6][C@H:7]1[CH2:12][C@@H:11]([CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH2:10][N:9]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:8]1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:24]=[C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22](=[O:23])[N:14]1[CH2:13][C@H:11]1[CH2:12][C@@H:7]([OH:6])[CH2:8][N:9]([C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131729310HCID 131729310, compound

Product 1

HCID 131729315HCID 131729315, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To cis-phenylmethyl (3RS,5SR)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-piperidinecarboxylate (for a preparation, see Example 134(e)) (0.92 g, 1.8 mmol) in 10 mL of THF at 0° C. was added a 1N solution of tetrabutyl ammonium fluoride in THF (4 mL, 4.0 mmol). The reaction was allowed to stir under nitrogen while warming to room temperature over 2 h. The reaction was partitioned between EtOAc and saturated aqueous NH4Cl. The organic phase was separated and washed with saturated aqueous NaHCO3, and brine, dried over Na2SO4, and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel using a 5-100% EtOAc/hexanes gradient to provide the desired compound (380 mg; 54%) as a colorless oil.

Workup

  1. customat 0° C.
  2. customThe reaction was partitioned between EtOAc and saturated aqueous NH4Cl
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by chromatography on silica gel using a 5-100% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-2c66151fb6ce4eb7925dec8ae54a615a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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