Ethyl Acetate → HCID 59444282, compound

HRID 1888125Notes

Reaction equation

HRID 1888125 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:33])[CH2:13][CH2:12][N:11]([C:14]([C@@H:16]([CH:28]([CH3:30])[CH3:29])[CH2:17][NH:18]C(=O)OCC[Si](C)(C)C)=[O:15])[CH2:10][C:9]2([CH3:32])[CH3:31])=[CH:4][CH:3]=1.ClC1C=CC(C(NC(C(C)C)CC(N2CC[C@@](C3C=CC(Cl)=CC=3)(O)C(C)(C)C2)=O)=O)=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CCOC(C)=O>C1COCC1>[NH2:18][CH2:17][C@H:16]([CH:28]([CH3:30])[CH3:29])[C:14]([N:11]1[CH2:12][CH2:13][C@@:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([OH:33])[C:9]([CH3:31])([CH3:32])[CH2:10]1)=[O:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57889125HCID 57889125, compoundHCID 59444220HCID 59444220, compound

Product 1

HCID 59444282HCID 59444282, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(trimethylsilyl)ethyl(S)-2-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine-1-carbonyl)-3-methylbutylcarbamate (110 mg, 0.221 mmol) in THF (1 mL) was added 1 equivalent of 1 M-tetra-N-butylammonium fluoride (0.221 mL, 0.221 mmol). The resulting mixture was stirred at room temperature for 1.5 hrs. After this time, the reaction was analyzed by LC/MS, which showed that the reaction was very slow. An additional 4 equiv. of TBAF (0.88 ml) was added and the mixture was stirred at room temperature for an additional 24 hour. After this time, the reaction mixture was added to EtOAc, washed with water and brine, dried over Na2SO4 and evaporated to give an oily residue. The oily residue was purified by Combiflash chromatography (24 g silica gel) with elution by 6:4 EtOAc-hexane to give the title compound (85.3 mg). MS (ESI+)=353.13 (M+H)+

Workup

  1. stirringthe mixture was stirred at room temperature for an additional 24 hour
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto give an oily residue
  6. customThe oily residue was purified by Combiflash chromatography (24 g silica gel) with elution by 6:4 EtOAc-hexane

Sources & evidence

ORD record
ord-b65e44252c7c4e53a0e6746e49f20de3
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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