tert-butyl 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]piperazine-1-carboxylate synthesis
- Product Name:tert-butyl 4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]piperazine-1-carboxylate
- CAS Number:1010925-33-3
- Molecular formula:C19H23N3O5
- Molecular Weight:373.4
85-41-6
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Yield:1010925-33-3 67%
Reaction Conditions:
with tetra-(n-butyl)ammonium iodide;N-ethyl-N,N-diisopropylamine in dichloromethane at 40; for 24 h;
Steps:
Phthalimide (33 mg, 0.23 mmol) was treated with fe/f-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 CH2CI2 (10 ml_) for 24 h at 40 °C. The mixture was partitioned between CH2CI2 and water. The organic phase was separated, dried over MgS04, 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). white solid; TLC (EtOAc/hexane = 1 : 1 ) Rf = 0.2; 1 H NMR (400 MHz, CDCI3) δ 7.85-7.87 (2 H, m), 7.70-7.72 (2 H, m), 4.49 (2 H, s), 3.51-3.57 (6 H, m), 3.44 (2 H, d, J = 5.2 Hz), 1 .46 (9 H, d, J = 4.8 Hz).
References:
WO2012/72019,2012,A1 Location in patent:Page/Page column 71
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