Diethyl Ether → Tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

HRID 47339

반응식

HRID 47339 반응식
[CH2:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(OCC)C.[Cl:20][C:21](Cl)([Cl:25])[C:22](Cl)=[O:23].C(=O)(O)[O-].[Na+]>C(COC)OC.[Cu].[Zn]>[Cl:20][C:21]1([Cl:25])[C:2]2([CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:1][C:22]1=[O:23]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 27568081-Boc-4-Methylenepiperidine

생성물 1

HCID 9857764Tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate수율 81.1%

시약·촉매·용매 2

HCID 10290809Zinc copper couple촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

49.3 g of tert-butyl 4-methylene-1-piperidine carboxylate was added to a mixture of 157.2 g zinc-copper alloy and 500 ml diethyl ether, and 900 ml solution of 181.8 g trichloroacetyl chloride in dimethoxyethane was added dropwise thereinto over 5.5 hours. After stirred for 30 min, the reaction solution was cooled and saturated aqueous sodium bicarbonate was added thereto at 0° C. or less. The mixture was filtered through Celite and evaporated. The resulting residue was extracted with ethyl acetate. The extract was washed with 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 62.5 g of tert-butyl 1,1-dichloro-2-oxo-7-azaspiro[3.5]nonane-7-carboxylate.

후처리

  1. temperaturethe reaction solution was cooled
  2. customat 0° C. or less
  3. filtrationThe mixture was filtered through Celite
  4. customevaporated
  5. extractionThe resulting residue was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-686052dff0074236bc1ad47101bb61b1
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699870B2

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