Hydrochloric Acid → 2-Aza-2-benzyl-4-oximino-3-oxo-bicyclo[3,2,1]octane

HRID 411332ノート

反応式

HRID 411332 の反応式
[CH2:1]([CH:8]1[C:14](=[O:15])[CH2:13][CH:12]2[CH2:16][CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CC([O-])(C)C.[K+].C1COCC1.[N:28](OCCC(C)C)=[O:29].Cl>C1COCC1>[CH2:1]([CH:8]1[C:14](=[O:15])[C:13](=[N:28][OH:29])[CH:12]2[CH2:16][CH:9]1[CH2:10][CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 223126692-Aza-2-benzyl-3-oxo-bicyclo[3,2,1]octaneHCID 66863523KOtBu THF

生成物 1

HCID 865849682-Aza-2-benzyl-4-oximino-3-oxo-bicyclo[3,2,1]octane収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-aza-2-benzyl-3-oxobicyclo[3.2.1]octane in THF was added 2.5 eq. of 1M t-BuOK/THF (Aldrich) and the resulting mixture was stirred for 30 minutes. Isoamyl nitrite (1.5 eq.) was then added dropwise and the reaction mixture was stirred overnight. To the reaction mixture was added 3N HCl and this mixture was extracted with ethyl acetate and the organic extracts washed with water, dried, and concentrated under reduced pressure. The residue was triturated with ether/hexanes, the solvents decanted and the residue dried under reduced pressure to afford 2-aza-2-benzyl-4-oximino-3-oxobicyclo[3.2.1]octane as a tan liquid (41% yield). This procedure is further described in Y. Kim, Tetrahedron Lett. 30(21), 2833-2636 (1989).

後処理

  1. stirringthe reaction mixture was stirred overnight
  2. extractionthis mixture was extracted with ethyl acetate
  3. washthe organic extracts washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with ether/hexanes
  7. customthe solvents decanted
  8. customthe residue dried under reduced pressure

出典と根拠

ORDレコード
ord-9a29c0e3faf34320a7c3d3431925280c
出典データセット
uspto-grants-2003_05
特許番号
US06559141B2

反応ノート

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