Triethylamine → 2,2,2-Trifluoro-1-(9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

HRID 471067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471067
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][OH:12])[CH:6]=[C:7]([F:9])[CH:8]=1.FC(F)(F)C(O)=O.[F:20][C:21]([F:36])([F:35])[C:22]([N:24]1[CH2:29][C:28]2([CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[O:27][CH2:26][CH2:25]1)=[O:23].C(N(CC)CC)C>C(#N)C>[F:36][C:21]([F:20])([F:35])[C:22]([N:24]1[CH2:29][C:28]2([CH2:34][CH2:33][N:32]([CH2:2][C:3]3[CH:4]=[C:5]([CH2:10][CH2:11][OH:12])[CH:6]=[C:7]([F:9])[CH:8]=3)[CH2:31][CH2:30]2)[O:27][CH2:26][CH2:25]1)=[O:23]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 579893452-(3-(Bromomethyl)-5-fluorophenyl)ethanolHCID 866367502,2,2-Trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate

Produkt 1

HCID 579893802,2,2-Trifluoro-1-(9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 2-(3-(bromomethyl)-5-fluorophenyl)ethanol (example 41, step b) (3.6 g) and 2,2,2-trifluoro-1-(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone trifluoroacetate (example 12, step d) (5.66 g) in acetonitrile (80 mL) was treated with triethylamine (5.38 mL) and the mixture stirred at 20° C. for 20 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 2.5% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 4.9 g.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-dc5d9a6b5a3c442bada883255e855e41
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

Notizen zur Reaktion

Wird geladen…