Ethyl Acetate → HCID 57937535, compound

HRID 1435133Notes

Reaction equation

HRID 1435133 reaction equation
CC([Si](C)(C)[O:6][CH:7]([C:9]1[N:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:12]=[CH:11][CH:10]=1)[CH3:8])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].CCOC(C)=O>C1COCC1>[OH:6][CH:7]([C:9]1[N:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]2)[CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57937601HCID 57937601, compound

Product 1

HCID 57937535HCID 57937535, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(+/−)-1,1-Dimethylethyl 4-{[6-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-2-pyridinyl]oxy}-1-piperidinecarboxylate (1.16 g, 2.66 mmol) was dissolved in 25 mL of THF with stirring, Tetrabutyammonium fluoride (3.20 mL, 1M in THF, 3.20 mmol) was added via syringe. The reaction was stirred for 1 h and poured Into saturated ammonium chloride solution and EtOAc. The layers were separated, and the organic layer was washed with brine. The combined aqueous layers were extracted with EtOAc. The combined organic layers were dried over MgSC4, filtered, and concentrated in vacuo. Purification by flash chromatography gave 0.810 g (94%) of the title compound. 1H MMR (300 MHz, DMSO-d6) δ 7.69 (dd, J=8.1, 7.3 Hz, 1H), 7.08 (d, J=7.3 Hz, 1H), 6.64 (d, J=8.1 Hz, 1H), 5.28 (d, J=4.9 Hz, 1H), 5.18 (m, 1H), 4.62 (m, 1H), 3.75-3.63 (m, 2H), 3.29-3.15 (m, 2H), 2.03-1.91 (m, 2H), 1.66-1.50 (m, 2H), 1.44 (s, 9H), 1.87 (d, J=6.5 Hz, 3H).

Workup

  1. stirringThe reaction was stirred for 1 h
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. extractionThe combined aqueous layers were extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSC4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-484a357e82a1403caa8bd0f46a277729
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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