Triethylamine → 2,2,2-Trifluoro-1-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

HRID 1689223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689223
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.FC(F)(F)C(O)=O.[F:26][C:27]([F:42])([F:41])[C:28]([N:30]1[CH2:35][C:34]2([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[O:33][CH2:32][CH2:31]1)=[O:29]>C(#N)C>[F:42][C:27]([F:26])([F:41])[C:28]([N:30]1[CH2:35][C:34]2([CH2:40][CH2:39][N:38]([CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][OH:11])[CH:4]=3)[CH2:37][CH2:36]2)[O:33][CH2:32][CH2:31]1)=[O:29]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 866367502,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

Produkt 1

HCID 579889742,2,2-Trifluoro-1-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 2-(3-(bromomethyl)phenyl)ethanol (example 6, step a) (0.223 g) dissolved in acetonitrile (1 mL) was added dropwise to a stirred solution of triethylamine (0.318 mL) and 2,2,2-trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate (example 12, step d) (0.38 g) in acetonitrile (2 mL) at 20° C., over a period of 2 minutes. The resulting mixture was stirred at 20° C. for 3 hours. The solvent was evaporated off and residue partitioned between dichloromethane and water, the aqueous layer was re-extracted twice with DCM and the combined organics were dried over sodium sulfate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography eluting with 6% methanol and 1% triethylamine in dichloromethane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.260 g.

Aufarbeitung

  1. customThe solvent was evaporated off
  2. customresidue partitioned between dichloromethane and water
  3. extractionthe aqueous layer was re-extracted twice with DCM
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified by flash silica chromatography
  8. washeluting with 6% methanol and 1% triethylamine in dichloromethane
  9. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-356fdd5a507e4f37890c0283c06560d4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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