Hydrochloric Acid → Methyl-2-dimethylcarbamoyl-1-(methoxycarbonylmethyl)piperidine-4-carboxylate

HRID 1458896ノート

反応式

HRID 1458896 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH:6]=1)=[O:4].Cl.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[K+].[K+]>CO.C1(C)C=CC=CC=1.[Pt]=O.O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:7]([C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH2:6]1)=[O:4]

参加物

9

反応物 4

HCID 313Hydrochloric Acid2 回HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 22097574Methyl 2-(dimethylcarbamoyl)pyridine-4-carboxylate

生成物 1

HCID 22097566Methyl-2-dimethylcarbamoyl-1-(methoxycarbonylmethyl)piperidine-4-carboxylate収率 96,296.297%

試薬・触媒・溶媒 4

HCID 82844Platinum oxide (PtO)触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

A mixture of compound 28 (55.4 g, 0.27 mmole), conc. HCl (16 ml) in MeOH (62 ml) was hydrogenated over platinum oxide (1 g) at 8 kg/cm2 for 24 hours. The catalyst was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting oil was used without further purification. A mixture of crude intermediate compound hydrochloride, methyl bromoacetate (61 g, 0.4 mole) and K2CO3 (73.5 g, 0.53 mole) in toluene (200 ml) was heated at 70° C. for 3 hours. After cooling the reaction mixture, H2O (200 ml) was added and extracted with EtOAc (200 ml×2). The combined organic extracts were dried over MgSO4 and concentrated down. The crude oil was purified by silica gel chromatography EtOAc as eluent to give 29 (69.8 g, 0.26 mole, 97%).

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting oil was used without further purification
  4. additionwas added
  5. extractionextracted with EtOAc (200 ml×2)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated down
  8. customThe crude oil was purified by silica gel chromatography EtOAc as eluent

出典と根拠

ORDレコード
ord-ffe36260347a4c0aadf7e5184a368b8f
出典データセット
uspto-grants-1998_12
特許番号
US05852038

反応ノート

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