Beta-Alanine → Diisopropyl Ether

HRID 623195노트

반응식

HRID 623195 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][C:12](=O)[CH2:13]3)=[CH:5][CH:4]=1.[CH2:18]([O:20][C:21](=[O:25])[CH2:22][C:23]#[N:24])[CH3:19].N1[CH2:31][CH2:30][CH2:29]CC1.NCCC(O)=O>CN(C)C=O.CCOCC>[C:23]([C:22](=[C:13]1[CH2:12][CH2:11][CH:10]2[N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:14]1[CH2:15][CH2:16]2)[C:21]([O:20][CH2:18][CH3:19])=[O:25])#[N:24].[CH:3]([O:2][CH:30]([CH3:29])[CH3:31])([CH3:8])[CH3:4]

참가 물질

8

반응물 4

HCID 239Beta-AlanineHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 189196618-(4-Methoxyphenyl)-8-azabicyclo[3.2.1]octan-3-one

생성물 2

HCID 7914Diisopropyl EtherHCID 54533282HCID 54533282, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

3.0 g of 8-(4-methoxyphenyl)-8-azabicyclo[3.2.1]octan-3-one were dissolved in 6 ml of dimethylformamide and treated with 1.8 ml of cyanoacetic acid ethyl ester, 0.2 ml of piperidine and 58 mg of β-alanine. The mixture was heated to 50° for 28 hours while stirring. After cooling to room temperature, the mixture was diluted with ether, washed four times with water, dried over sodium sulfate and concentrated under reduced pressure. Chromatography of the residue on 250 g of silica gel with hexane/ethyl acetate (3:2) yielded ethyl cyano-[8-(4-methoxyphenyl)-8-azabicyclo[3.2.1]octanylidene]acetate as a white solid, melting point 121°-122° (from isopropyl ether).

후처리

  1. temperatureThe mixture was heated to 50° for 28 hours
  2. washwashed four times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3ee0b437a1b54f358c7b921bd2929d9d
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04774249

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