Sodium hydride → 1-t-Butyloxycarbonyl-4-[(3-phenyl-2-propynyloxy)ethyl]piperidine

HRID 1034418

반응식

HRID 1034418 반응식
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][CH2:27]Cl)=[CH:21][CH:20]=1>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][O:18][CH2:27][C:26]#[C:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 287343(3-Chloroprop-1-yn-1-yl)benzeneHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

생성물 1

HCID 538709501-t-Butyloxycarbonyl-4-[(3-phenyl-2-propynyloxy)ethyl]piperidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

Sodium hydride (0.912 g, 23 mmol, 60% oil disp.) which had been rinsed with hexanes (3×10 mL), and dry N,N-dimethylformamide (50 mL) were cooled to 0° C. with stirring under a nitrogen atmosphere. A solution of 1-t-butyloxycarbonyl-4-hydroxyethylpiperidine (4.3 g, 19 mmol) in dry DMF (15 mL) was added, and the mixture stirred for 1 hour. 3-Phenylpropargyl chloride (2.8 g, 19 mmol) was added, and the mixture was heated to reflux for 24 hours. After cooling, the solvent was removed by distillation under reduced pressure. The residue was u dissolved in ethyl acetate and extracted with water (3×100 mL), brine (100 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with 5% ethyl acetate in hexanes, and concentrated under reduced pressure to yield 1-t-butyloxycarbonyl-4-[(3-phenyl-2-propynyloxy)ethyl]piperidine (1.02 g, 16% dark oil. 1H NMR (300 MHz, CDCl3 /TMS, δ): 7.5(m,2H),

후처리

  1. stirringthe mixture stirred for 1 hour
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 24 hours
  4. temperatureAfter cooling
  5. customthe solvent was removed by distillation under reduced pressure
  6. dissolutiondissolved in ethyl acetate
  7. extractionextracted with water (3×100 mL), brine (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by chromatography on silica gel
  12. washeluting with 5% ethyl acetate in hexanes
  13. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e506bfc9bb4e4730a773708eee30cf8e
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05317024

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