Ammonium Chloride → Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

HRID 47340

반응식

HRID 47340 반응식
Cl[C:2]1(Cl)[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:18].[Cl-].[NH4+]>CO.[Zn]>[O:18]=[C:3]1[CH2:2][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4]1

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 9857764Tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

생성물 1

HCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate수율 80.2%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

106.1 g zinc dust was added to a mixture of 62.5 g tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate and 500 ml saturated ammonium chloride in methanol. The mixture was stirred for 1 hr and 20 min at room temperature and filtered through Celite. The filtrate was evaporated, 1 N hydrochloric acid/ethyl acetate was added thereto, and the organic layer was recovered. The extract was washed with water, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated, and the resulting residue was subjected to silica gel column chromatography to give 38.9 g of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate.

후처리

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated
  3. addition1 N hydrochloric acid/ethyl acetate was added
  4. customthe organic layer was recovered
  5. washThe extract was washed with water, saturated sodium bicarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-97e74cb0144947d491a5546620c3a145
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699870B2

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