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

HRID 604268노트

반응식

HRID 604268 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-46ee7f3081cf4b148f5a4eb4b9e5c78a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910585B2

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