Ammonia → 2-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol

HRID 1689373

Reaktionsgleichung

Reaktionsgleichung von HRID 1689373
N.FC(F)(F)C([N:6]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][OH:26])[C:19]=3[F:27])[CH2:13][CH2:12]2)[O:9][CH2:8][CH2:7]1)=O>CO>[O:9]1[C:10]2([CH2:16][CH2:15][N:14]([CH2:17][C:18]3[C:19]([F:27])=[C:20]([CH2:24][CH2:25][OH:26])[CH:21]=[CH:22][CH:23]=3)[CH2:13][CH2:12]2)[CH2:11][NH:6][CH2:7][CH2:8]1

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 579893822,2,2-Trifluoro-1-(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

Produkt 1

HCID 579891872-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

‘880’ Aqueous ammonia solution (5 mL) was added to a solution of 2,2,2-trifluoro-1-(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone (example 67, step e) (1.9 g) in methanol (25 mL). The resulting mixture was stirred for 90 min and the solvent evaporated. The residue was purified by silica gel chromatography eluting with 94.5:5:0.5 to 89:10:1 DCM:methanol:‘880’ ammonia gradient. The fractions containing product were combined and evaporated to give a gum that solidified on standing. The white solid was triturated with isohexane and dried over sodium sulphate to give the subtitled compound as a white solid. Yield 1 g.

Aufarbeitung

  1. customthe solvent evaporated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with 94.5:5:0.5 to 89:10:1 DCM
  4. additionThe fractions containing product
  5. customevaporated
  6. customto give a gum that
  7. customThe white solid was triturated with isohexane
  8. dry with materialdried over sodium sulphate

Quellen und Nachweise

ORD-Eintrag
ord-42aaa5d94e8a4b079d124b54ccba12c9
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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