반응 #84633

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tert-Butyl 4-(2-(2,4-difluorophenyl)acetyl)piperazine-1-carboxylate

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title compound

수율 100.3%

tert-Butyl 4-(2,4-Difluorophenethyl)piperazine-1-carboxylate

수율 100.3%

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONborane-tetrahydrofuran complex (1.0 M, 15.8 mL, 15.8 mmol) was added
2. 2
   기타The reaction was quenched slowly with methanol (0.4 mL) dropwise
3. 3
   workup.ADDITIONThen, 0.5 M HCl (10.0 mL) was added
4. 4
   추출the mixture was extracted with EtOAc (2×100 mL)
5. 5
   건조The organic extracts were dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to give a residue that
9. 9
   기타was purified by RP-HPLC
10. 10
    workup.ADDITIONThe best fractions were added to NaHCO3 (20 mL)
11. 11
    추출extracted with EtOAc (2×100 mL)
12. 12
    건조The organic extracts were dried over Na2SO4
13. 13
    여과filtered
14. 14
    농축concentrated

실험 절차

tert-Butyl 4-(2-(2,4-difluorophenyl)acetyl)piperazine-1-carboxylate (1.12 g, 3.30 mmol) was dissolved in THF (8.5 mL) and borane-tetrahydrofuran complex (1.0 M, 15.8 mL, 15.8 mmol) was added. The reaction was refluxed at 66° C. The reaction was quenched slowly with methanol (0.4 mL) dropwise. Then, 0.5 M HCl (10.0 mL) was added, and the mixture was extracted with EtOAc (2×100 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated to give a residue that was purified by RP-HPLC. The best fractions were added to NaHCO3 (20 mL) and extracted with EtOAc (2×100 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated to yield the title compound (1.08 g) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 1.41 (s 9H), 2.80-2.96 (m, 6H), 3.10-3.03 (m, 2H), 3.50-3.60 (m, 4H), 7.06 (dt, J=2.6, 8.5 Hz, 1H), 7.22 (dt, J=2.6, 9.6 Hz, 1H), 7.38-7.46 (m, 1H). Exact mass calculated for C17H24F2N2O2: 326.2. Found: LCMS m/z=327.1 (M+H+).

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