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

HRID 923647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923647
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4ef059a068b84f648e308c16e253ed43
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278982B2

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