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p-Fluoronitrobenzene → Tert-butyl 4-((4-nitrophenyloxy)methyl)piperidine-1-carboxylate

HRID 1079387
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HRID 1079387 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 516892Sodium BicarbonateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 23366891Tert-butyl 4-((4-nitrophenyloxy)methyl)piperidine-1-carboxylate수율 43.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-tert-Butyloxycarbonyl-4-hydroxymethylpiperidine (2.8 g) was dissolved in dimethylformamide (10 ml), followed by stirring for 30 minutes. To the mixture was added p-fluoronitrobenzene (2.1 g), followed by stirring at room temperature overnight. Aqueous saturated solution of sodium bicarbonate was added to the mixture which was extracted with methylene chloride (50 ml×3). The combined organic layer was washed with saturated saline and dried over sodium sulfate. The solvent was distilled off under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (developing solvent: hexane/ethylacetate=5/1 (v/v)) to obtain 1-tert-butyloxycarbonyl-4-[(4-nitrophenyloxy)methyl]piperidine (1.9 g) as pale yellow crystals, m.p. 130°-131° C.

후처리

  1. stirringby stirring at room temperature overnight
  2. extractionwas extracted with methylene chloride (50 ml×3)
  3. washThe combined organic layer was washed with saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by silica gel column chromatography (developing solvent: hexane/ethylacetate=5/1 (v/v))

출처 및 근거

ORD 기록
ord-367dea406add457db009002abaec1440
출처 데이터셋
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05580883

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