Hydroxyamine hydrochloride → 4-Cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl]cyclohexan-1-one oxime

HRID 2394511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2394511
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:12]([O:25][CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:11]=2)[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)#[N:2].Cl.[NH2:32][OH:33]>N1C=CC=CC=1>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:12]([O:25][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[CH:11]=2)[CH2:4][CH2:5][C:6](=[N:32][OH:33])[CH2:7][CH2:8]1)#[N:2]

Komponenten

4

Edukt 2

HCID 443297Hydroxyamine hydrochlorideHCID 152952054-Cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl)cyclohexan-1-one

Produkt 1

HCID 189736834-Cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl]cyclohexan-1-one oximeAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 4-cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl)cyclohexan-1-one (0.525 g, 1.49 mmol) and hydroxylamine hydrochloride (0.114 g, 1.63 mmol) in pyridine (5 mL) was was stirred at room temperature under an argon atmosphere for 18 h. The mixture was partitioned between 1N hydrochloric acid and methylene chloride, the organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 35% ethyl acetate/hexanes, provided a white solid (0.45 g, 82%): m.p. 55°-57° C.

Aufarbeitung

  1. customThe mixture was partitioned between 1N hydrochloric acid and methylene chloride
  2. extractionthe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. customthe solvent was removed in vacuo
  5. customPurification by flash chromatography
  6. washeluting with 35% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6866f5a5884f43549608a34ffabe2a24
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811455

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