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Sodium hydride → 1-Boc-4-(2-pyridyloxy)piperidine

HRID 23951
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HRID 23951 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl.Cl[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 156199202-Chloropyridine--hydrogen chloride (1/1)

생성물 1

HCID 219060391-Boc-4-(2-pyridyloxy)piperidine수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

1-t-Butoxycarbonyl-4-piperidinol (5.0 g 24.88 mmol) in dry dimethylformamide (60 ml) was treated with sodium hydride (60% 2.99 g 74.75 mmol) at room temperature under argon and then with 2-chloropyridine hydrochloride (4.1 g 27.33 mmol). Then mixture was heated at 80° C. overnight. After cooling the reaction was carefully quenched with water (5 ml) and then diluted with more water (20 ml) and extracted with ethyl acetate (30 ml). The organic solution was washed with sat. sodium bicarbonate, dried (MgSO4) and evaporated to give 1-t-butoxycarbonyl-4-(2-pyridoxy)piperidine (4.96 g 72%).

후처리

  1. temperatureAfter cooling the reaction
  2. customwas carefully quenched with water (5 ml)
  3. additiondiluted with more water (20 ml)
  4. extractionextracted with ethyl acetate (30 ml)
  5. washThe organic solution was washed with sat. sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-390aae966993417181c270dae2276020
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06855715B1

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