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

HRID 1900051ノート

反応式

HRID 1900051 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dbbda9003b584edf9f6a51c3d5e4b495
出典データセット
uspto-grants-1996_11
特許番号
US05574055

反応ノート

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