Sodium Methoxide → 8-Ethoxy-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

HRID 1022377

반응식

HRID 1022377 반응식
C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:26])[CH2:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[CH2:10][CH2:9][N:8]([O:11][CH2:12][CH3:13])[CH2:7][CH2:6]1)=O.C[O-].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[CH2:12]([O:11][N:8]1[CH2:9][CH2:10][C:5]2([NH:14][C:15](=[O:26])[C:16]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])=[C:3]2[OH:2])[CH2:6][CH2:7]1)[CH3:13]

참가 물질

5

반응물 2

HCID 10942334Sodium MethoxideHCID 596145921-Ethoxy-4-[2-(2,4,6-trimethyl-phenyl)-acetylamino]-piperidine-4-carboxylic acid methyl ester

생성물 1

HCID 596145818-Ethoxy-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one수율 24.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
65 °C

실험 절차

To a solution of 2.3 g of 1-ethoxy-4-[2-(2,4,6-trimethyl-phenyl)-acetylamino]-piperidine-4-carboxylic acid methyl ester in 26 ml of dimethylformamide is added 3 g of sodium methoxide. The reaction mixture is heated to 65° C. and stirred for 5 hours. The reaction mixture is poured into brine, neutralized and extracted with ethyl acetate. The organic phase is washed with brine, dried with sodium sulfate, filtered and concentrated. The residue is subjected to column chromatography (heptane/ethyl acetate 2:1) to yield 510 mg of 8-ethoxy-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one as a solid, mp: >250° C.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ffdf53a0b4db4e33b98754217bd6a43d
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722578B2

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