Dimethyl Sulfoxide → Methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate

HRID 1801585

反応式

HRID 1801585 の反応式
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH3:28])=[O:26])[CH2:21][CH2:20]1.CS(C)=O>CCOC(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH3:28])=[O:26])[CH2:21][CH2:20]2)=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)=[O:7]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 855054-Chloro-3-nitrobenzaldehydeHCID 424914Methyl isonipecotate

生成物 1

HCID 9111291Methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate収率 43.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 4-chloro-3-nitrobenzaldehyde 57 (5.099 g, 27 mmol), cesium carbonate (9.48 g, 29 mmol), and methyl piperidine-4-carboxylate (4 mL, 27 mmol) was added DMSO (27 mL). The reaction mixture was heated to 100° C. for 30 min and diluted with EtOAc. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 30% to 50% EtOAc in hexanes) gave methyl 1-(4-formyl-2-nitrophenyl)piperidine-4-carboxylate 58 (3.45 g, 43% yield) as a yellow oil. Mass spectrum: calculated for C14H16N2O5 292.1. found 293.1 (M++1).

後処理

  1. washThe organic phase was washed with water (2×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash column chromatography on silica gel (eluted with 30% to 50% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-6a1c2fc5105048648d90d137b877ecb4
出典データセット
uspto-grants-2013_01
特許番号
US08349831B2

関連ノート

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