Npc164516 → 8-Azabicyclo[3.2.1]octan-3-one, 8-methyl-, oxime

HRID 506224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506224
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5](=O)[CH2:6]2.Cl.[NH2:12][OH:13]>C(O)C>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5](=[N:12][OH:13])[CH2:6]2

Komponenten

4

Edukt 2

HCID 79038Npc164516HCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 27280758-Azabicyclo[3.2.1]octan-3-one, 8-methyl-, oximeAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A 500-mL one-neck round-bottomed flask equipped with a magnetic stirrer was charged with 8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (5.00 g, 35.9 mmol), hydroxylamine hydrochloride (7.08 g, 102 mmol) sodium acetate (39.0 g, 476 mmol) and ethanol (45 mL). After stirring at ambient temperature for 4 h, the reaction mixture was evaporated to a solid residue. This residue was triturated with ethyl acetate (200 mL) and filtered. Evaporation of the filtrate to dryness gave 5.08 g (93% yield) of 8-methyl-8-aza-bicyclo[3.2.1]octan-3-one oxime as a white solid: mp 140-142° C.; 1H NMR (300 MHz, CD3OD) δ 3.76 (m, 2H), 3.33-3.23 (m, 2H), 2.75 (m, 1H), 2.69 (s, 3H), 2.46-2.14 (m, 4H), 1.88-1.66 (m, 2H); MS (APCI) m/z 155 [M+H]+.

Aufarbeitung

  1. customA 500-mL one-neck round-bottomed flask equipped with a magnetic stirrer
  2. customthe reaction mixture was evaporated to a solid residue
  3. customThis residue was triturated with ethyl acetate (200 mL)
  4. filtrationfiltered
  5. customEvaporation of the filtrate to dryness

Quellen und Nachweise

ORD-Eintrag
ord-472f7c8b4cf74bbfa1799fb56cce75b3
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781430B2

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