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

HRID 1079387
ノート
印刷プレビュー

反応式

HRID 1079387 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-367dea406add457db009002abaec1440
出典データセット
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05580883

反応ノート

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