N-acetonyl-8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxamide → 4-Isopropoxy-3-methylbenzaldehyde

HRID 73021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73021
C(NC(C1OC2(CCN([C:18](=[O:30])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH3:29])[CH:20]=3)CC2)CN(CC2C=CC=CC=2)C1)=O)C(C)=O>C1COCC1>[CH:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([CH:18]=[O:30])=[CH:20][C:21]=1[CH3:29])([CH3:28])[CH3:27]

Komponenten

3

Edukt 1

HCID 70872809N-acetonyl-8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxamide

Produkt 1

HCID 509982434-Isopropoxy-3-methylbenzaldehydeAusbeute 164 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To N-acetonyl-8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxamide (136 mg, 0.26 mmol) in THF (3 mL) was added Burgess' Salt (155 mg, 0.65 mmol) and the reaction mixture was heated at 75° C. in a sealed vial for 2 hours. The solvents were removed under reduced pressure, and the residue was dissolved in DMF (1 mL), filtered and purified by Waters preparative LC/MS (1-99% ACN/H2O (5 mM HCl)). The desired fractions were concentrated in vacuo and the residue partitioned between EtOAc/saturated aqueous NaHCO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to yield 8-benzyl-10-(5-methyloxazol-2-yl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (76 mg, 58%) as a foam. ESI-MS m/z calc. 503.6. Found 504.5 (M+1)+; Retention time: 1.74 minutes (3 min run).

Aufarbeitung

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in DMF (1 mL)
  3. filtrationfiltered
  4. custompurified by Waters preparative LC/MS (1-99% ACN/H2O (5 mM HCl))
  5. concentrationThe desired fractions were concentrated in vacuo
  6. customthe residue partitioned between EtOAc/saturated aqueous NaHCO3 solution
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted with EtOAc (2×)
  9. dry with materialThe combined organics were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-499a0e9ff92d40a482c4a7714ed2a2a1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828996B2

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