반응 #2161269

반응 방정식

NaBH(OAc)3

1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine

acetone

→

title compound

수율 57.4%

1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}-N-isopropylpiperidin-4-amine

수율 57.4%

용매

CH2Cl2

NaOH

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred overnight at room temperature
2. 2
   workup.STIRRINGthe bi-phasic solution was stirred for 20 minutes
3. 3
   추출The mixture was extracted with CH2Cl2 (2×25 mL)
4. 4
   건조the combined organic layers were dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH)

실험 절차

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}piperidin-4-amine (0.3 g, 0.76 mmol) in CH2Cl2 (5 mL) was added acetone (56 μL, 0.76 mmol) and the solution was stirred for 15 minutes at room temperature. This was followed by the addition of NaBH(OAc)3 (0.242 g, 1.14 mmol) and the reaction mixture was stirred overnight at room temperature. The mixture was diluted with CH2Cl2 (20 mL) and 2 M NaOH and the bi-phasic solution was stirred for 20 minutes. The mixture was extracted with CH2Cl2 (2×25 mL) and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH) to give the title compound as a white solid (0.19 g, 44%). 1H NMR (400 MHz, DMSO-D6) δ ppm 8.51 (d, 2 H), 7.66 (d, 2 H), 7.30 (t, 2 H), 7.14 (t, 2 H), 6.51 (s, 1 H), 5.13-5.20 (m, 2 H), 4.07-4.16 (m, 1 H), 3.93 (s, 2 H), 3.77-3.87 (m, 1 H), 3.04-3.14 (m, 1 H), 2.83-2.93 (m, 1 H), 2.69-2.79 (m, 2 H), 1.72-1.86 (m, 5H); m/z (APCI+) for C25H30N5OF 436.1 (M+H)+.

출처