Iodoethane → tert-Butyl 4-(3-(5-ethoxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

HRID 1666410노트

반응식

HRID 1666410 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1.[CH2:29](I)[CH3:30].C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.O>[CH2:29]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1)[CH3:30]

참가 물질

7

반응물 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 66875736tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

생성물 1

HCID 66876086tert-Butyl 4-(3-(5-ethoxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate수율 95.3%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

To a stirred solution of tert-butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.56 mmol) in acetone (5 mL) was added ethyl iodide (0.304 g, 1.96 mmol), K2CO3 (0.431 g, 3.12 mmol) and 18-crown-6 (0.824 g, 3.12 mmol) at 0° C. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate three times. The organic layer was washed with fresh water and brine solution, dried over Na2SO4 and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (1:19 acetone:hexanes) to give the title compound (610 mg, 95%). 1H NMR (500 MHz, CDCl3): δ 7.86 (d, J=2.5 Hz, 1H), 7.27 (m, 2H), 6.96 (d, J=7.5 Hz, 1H), 6.90 (m, 2H), 6.85 (d, J=9 Hz, 1H), 6.32 (s, 1H), 4.02 (q, 2H, J=6.8), 3.49 (s, 2H), 3.38 (s, 2H), 2.45 (s, 2H), 2.30 (s, 2H), 1.47 (s 9H) 1.40 (t, J=6.92 Hz, 3H); m/z (411.51, M+ H+).

후처리

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer was washed with fresh water and brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (1:19 acetone:hexanes)

출처 및 근거

ORD 기록
ord-ba906a94597f4b18bf835b6a87031900
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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