N-bromobutanimide → 5-Bromo-1-cyclohexylmethyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester

HRID 1410929ノート

反応式

HRID 1410929 の反応式
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6](=[C:11]([NH:13][CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH3:12])[C:7]([O:9][CH3:10])=[O:8].C[O-].[Na+].[Br:25]N1C(=O)CCC1=O>CO>[CH3:10][O:9][C:7]([C:6]1[CH:5]=[C:4]([Br:25])[C:3](=[O:2])[N:13]([CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:11]=1[CH3:12])=[O:8]

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 867141524-[1-(Cyclohexylmethyl-amino)-ethylidene]-pent-2-enedioic acid dimethyl ester

生成物 1

HCID 682971425-Bromo-1-cyclohexylmethyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester収率 67.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

MeOH (200 mL) was added to a flask containing 4-[1-(cyclohexylmethyl-amino)-ethylidene]-pent-2-enedioic acid dimethyl ester (6.3 g, 21.4 mmol). NaOMe solution (4.9 mL, 21.4 mmol, 4.375 M in MeOH) and N-bromosuccinimide (4.56 g, 25.6 mmol) were added, and the resulting mixture was refluxed for 1 h. After cooling to r.t., the solvent was evaporated in vacuo. Saturated NH4Cl was added, and the resulting mixture was extracted with CH2Cl2. The organic layer was dried over MgSO4 and concentrated. The crude product was chromatographed (20% EtOAc/hexanes) to give 4.95 g of the title compound. MS: (+) m/z 364.21, 366.16 (M+Na, 79/81Br).

後処理

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. customthe solvent was evaporated in vacuo
  3. additionSaturated NH4Cl was added
  4. extractionthe resulting mixture was extracted with CH2Cl2
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was chromatographed (20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-0b3f41bd76d04fd78351abfe0d7d3a5d
出典データセット
uspto-grants-2014_12
特許番号
US08921389B2

反応ノート

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