Hydrochloric Acid → 4-(7-Amino-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 604268ノート

反応式

HRID 604268 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]3[C:15]=2[CH2:16][N:17]([CH3:27])[C:18]3=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>C(O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]3[C:15]=2[CH2:16][N:17]([CH3:27])[C:18]3=[O:26])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 598491954-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 598491864-(7-Amino-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester収率 101%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (5.37 g, 14 mmol) in ethanol (200 mL), iron powder (3.98 g, 70 mmol) and 1N hydrogen chloride (28 mL) are added and the mixture is stirred at 60° C. for 2 hours. The mixture is cooled to room temperature, and then 1N sodium hydroxide (28 mL) is added. After removing insoluble material by filtration, the mixture is concentrated. The residue is extracted twice with dichloromethane. The organic layer is successively washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo to afford 4-(7-Amino-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (4.9 g) as pale green amorphous solids in 99% yield. Rf=0.18 (Hexane/AcOEt=111). 1H-NMR (400 MHz, CDCl3, δ, ppm): 1.49 (s, 9H), 2.85 (t, 4H), 3.13 (s, 3H), 3.54 (t, 4H), 4.28 (s, 2H), 5.03 (s, 2H), 6.56 (d, 1H), 6.96 (d, 1H).

後処理

  1. temperatureThe mixture is cooled to room temperature
  2. customAfter removing insoluble material
  3. filtrationby filtration
  4. concentrationthe mixture is concentrated
  5. extractionThe residue is extracted twice with dichloromethane
  6. washThe organic layer is successively washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-46ee7f3081cf4b148f5a4eb4b9e5c78a
出典データセット
uspto-grants-2011_03
特許番号
US07910585B2

反応ノート

読み込み中…