Ammonium Chloride → methyl 1-[(1,1-dimethylethoxy)carbonyl]hexahydro-7-oxo-beta-(2-propenyl)-1H-azepine-2-butanoate

HRID 849143노트

반응식

HRID 849143 반응식
[CH2:1]([Li])[CH:2]=[CH2:3].[CH3:5][O:6][C:7](=[O:26])[CH:8]=[CH:9][CH2:10][CH:11]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13](=[O:18])[N:12]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[Cl-].[NH4+]>C1COCC1.[Cu]I>[CH3:24][C:22]([CH3:23])([O:21][C:19]([N:12]1[C:13](=[O:18])[CH2:14][CH2:15][CH2:16][CH2:17][CH:11]1[CH2:10][CH:9]([CH2:3][CH:2]=[CH2:1])[CH2:8][C:7]([O:6][CH3:5])=[O:26])=[O:20])[CH3:25]

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 542261121,1-dimethylethyl hexahydro-2-(4-methoxy-4-oxo-2-butenyl)-7-oxo-1H-azepine-1-carboxylateHCID 178506856HCID 178506856, 화합물

생성물 1

HCID 18800746methyl 1-[(1,1-dimethylethoxy)carbonyl]hexahydro-7-oxo-beta-(2-propenyl)-1H-azepine-2-butanoate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Four equivalents of allyl lithium are added to a stirring suspension of 2 equivalents copper (I) iodide in THF at -50° C. under argon. After the mixtures becomes homogeneous (approx. 20 minutes.), a solution of the title ester of Example 209 (1 equivalent) in THF is added to the cold mixture and stirred below -50° C. for approx. 30 minutes. The mixture is poured into saturated ammonium chloride solution and stirred vigorously for 15 minutes. The mixture is then partitioned between ether and water and the organic layer is washed with water and brine before it is dried (Na2SO4). The mixture is then filtered and stripped of all solvent. The title material is then purified by column chromatography.

후처리

  1. custom(approx. 20 minutes.)
  2. stirringstirred vigorously for 15 minutes
  3. customThe mixture is then partitioned between ether and water
  4. washthe organic layer is washed with water and brine before it
  5. dry with materialis dried (Na2SO4)
  6. filtrationThe mixture is then filtered
  7. customThe title material is then purified by column chromatography

출처 및 근거

ORD 기록
ord-410f26e01ef342aba88a683bd1dd4816
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011028

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