Potassium Carbonate → 5-(1,3-Oxazol-2-yl)-1-azabicyclo[3.2.1]octane oxalate salt

HRID 654527

反応式

HRID 654527 の反応式
[N:1]12[CH2:8][C:5]([C:9]([NH2:11])=[O:10])([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[C:12]1(=O)[O:16][CH:15]=[CH:14][O:13]1.[C:18](=[O:21])([O-:20])[O-].[K+].[K+]>CCOCC>[C:12]([OH:16])(=[O:13])[C:18]([OH:20])=[O:21].[O:10]1[CH:15]=[CH:14][N:11]=[C:9]1[C:5]12[CH2:8][N:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 13385Vinylene carbonateHCID 198875881-Azabicyclo[3.2.1]octane-5-carboxamide

生成物 1

HCID 198875785-(1,3-Oxazol-2-yl)-1-azabicyclo[3.2.1]octane oxalate salt収率 16%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A stirred mixture of 1-azabicyclo[3.2.1]oct-5-ylcarboxamide (D20, 1.50 g, 0.0097 mole) and vinylene carbonate (1.2 g, 0.014 mole) in polyphosphoric acid (35 g) was heated at 120°-130° C. for 2h. The reaction mixture was allowed to cool, then treated with ice, before basifying with potassium carbonate solution. The aqueous was shaken well with ether, then the mixture filtered and the organic layer separated. The aqueous was again extracted with ether (2×80 ml) and all the ether extracts combined, dried (Na2SO4) and concentrated in vacuo to leave a yellow oil. This was chromatographed on a basic alumina column eluting with ethyl acetate and the material obtained converted to its oxalate salt and recrystallised from methanol/ether to give the title compound (E12) as a white solid (410 mg, 16%) m.p. 143°-145° C.

後処理

  1. temperaturewas heated at 120°-130° C. for 2h
  2. temperatureto cool
  3. additiontreated with ice
  4. filtrationthe mixture filtered
  5. customthe organic layer separated
  6. extractionThe aqueous was again extracted with ether (2×80 ml) and all the ether
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto leave a yellow oil
  10. customThis was chromatographed on a basic alumina column
  11. washeluting with ethyl acetate
  12. customthe material obtained
  13. customrecrystallised from methanol/ether

出典と根拠

ORDレコード
ord-e74371503dec42b8bb8460ca93b88ad0
出典データセット
uspto-grants-1992_07
特許番号
US05132316

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