Phthalimide → tert-butyl 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]piperazine-1-carboxylate

HRID 923647노트

반응식

HRID 923647 반응식
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.Cl[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15].C(N(C(C)C)CC)(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[O:6]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:11])[N:5]1[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15]

참가 물질

6

반응물 3

HCID 6809PhthalimideHCID 81531DiisopropylethylamineHCID 15829156Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate

생성물 1

HCID 24281265tert-butyl 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]piperazine-1-carboxylate수율 67%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6344Dichloromethane용매

실험 절차

Phthalimide (33 mg, 0.23 mmol) was treated with tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate (80.5 mg, 0.32 mmol), tetrabutylammonium iodide (TBAI, 84 mg, 2.3 mmol), diisopropylethylamine (DIEA, 0.20 mg, 1.14 mmol) in anhydrous CH2Cl2 (10 mL) for 24 h at 40° C. The mixture was partitioned between CH2Cl2 and water. The organic phase was separated, dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:1) to give the title compound (57.1 mg, 67% yield). C19H23N3O5; white solid; TLC (EtOAc/hexane=1:1) Rf=0.2; 1H NMR (400 MHz, CDCl3) δ 7.85-7.87 (2H, m), 7.70-7.72 (2H, m), 4.49 (2H, s), 3.51-3.57 (6H, m), 3.44 (2H, d, J=5.2 Hz), 1.46 (9H, d, J=4.8 Hz).

후처리

  1. customThe mixture was partitioned between CH2Cl2 and water
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:1)

출처 및 근거

ORD 기록
ord-4ef059a068b84f648e308c16e253ed43
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278982B2

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