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

HRID 411332노트

반응식

HRID 411332 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a29c0e3faf34320a7c3d3431925280c
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559141B2

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