Dimethylformamide → tert-Butyl 7-cyano-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

HRID 33199노트

반응식

HRID 33199 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17](OS(C(F)(F)F)(=O)=O)=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][N:28](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([C:27]#[N:28])=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 181732813-(tert-butoxycarbonyl)-7-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine

생성물 1

HCID 18173275tert-Butyl 7-cyano-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate수율 23%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3-(tert-butyloxycarbonyl)-7-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-3-benzazepine (4.78 g, 12.1 mmol), zinc cyanide (1.42 g, 15.6 mmol) and tetrakis-triphenylphosphine palladium (0) (1.4 g, 1.2 mmol, 10 mol %), in dry dimethylformamide (50 ml) was stirred at 100° C. for 3 h under argon. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (120 ml) and filtered. The filtrate was washed with saturated aqueous sodium bicarbonate (100 ml), then water (2×50 ml), then brine (50 ml). The organic layer was dried over sodium sulfate and evaporated in vacuo to give brown oil, which was purified by chromatography on silica gel with 20-100% ethyl acetate—hexane elution to give the title compound (0.765 g, 23%) as a brown oil.

후처리

  1. filtrationfiltered
  2. washThe filtrate was washed with saturated aqueous sodium bicarbonate (100 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated in vacuo
  5. customto give brown oil, which
  6. customwas purified by chromatography on silica gel with 20-100% ethyl acetate—hexane elution

출처 및 근거

ORD 기록
ord-80acd03965e04733a86ece3b6b9d8861
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429579B2

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