Dichloromethane → (RS)-5-methoxymethyl-3-[4-(4-oxo-piperidin-1-yl)-phenyl]-oxazolidin-2-one

HRID 1900051노트

반응식

HRID 1900051 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14]C(=O)OCC)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH3:20][O:21][CH2:22][CH:23]1[CH2:27]O[C:25](=[O:28])[O:24]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O>[CH3:20][O:21][CH2:22][CH:23]1[O:24][C:25](=[O:28])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([N:5]3[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][CH2:6]3)=[CH:9][CH:10]=2)[CH2:27]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-oneHCID 23371821Ethyl 4-(4-oxo-piperidin-1-yl)-phenylcarbamate

생성물 1

HCID 23371896(RS)-5-methoxymethyl-3-[4-(4-oxo-piperidin-1-yl)-phenyl]-oxazolidin-2-one수율 8.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
160 °C

실험 절차

A mixture of 6.0 g of ethyl 4-(4-oxo-piperidin-1-yl)-phenylcarbamate, 5.0 g of 4-methoxymethyl-1,3-dioxolan-2-one and 0.6 g of potassium carbonate was heated to 160° C. under argon for 3 h. The reaction mixture was cooled, treated with methylene chloride and water and the phases were separated. The organic phase was dried with magnesium sulfate and concentrated. The residue (7.8 g) was chromatographed over silica gel 60 using ethyl acetate as the eluent. There was obtained 0.6 g of (RS)-5-methoxymethyl-3-[4-(4-oxo-piperidin-1-yl)-phenyl]-oxazolidin-2-one. 1H-nmr (CDCl3) ppm: 7.46 (d, 2H), 6.98 (d, 2H), 4.76 (m, 1H), 3.99 (t, 1H), 3.88 (t, 1H), 3.64 (d, 2H), 3.57 (t, 4H), 3.44 (s, 3H), 2.56 (t, 4H).

후처리

  1. temperatureThe reaction mixture was cooled
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue (7.8 g) was chromatographed over silica gel 60 using ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-dbbda9003b584edf9f6a51c3d5e4b495
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05574055

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