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Sodium hydride → tert-Butyl 4-(2-chloro-5-fluoro-4-nitrobenzylidene)piperidine-1-carboxylate

HRID 515301
ノート
印刷プレビュー

反応式

HRID 515301 の反応式
[Cl:1][C:2]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([F:20])=[CH:13][C:3]=1[CH2:4]P(=O)(OCC)OCC.O=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([F:20])=[CH:13][C:3]=1[CH:4]=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1
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 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 86670949Diethyl 2-chloro-5-fluoro-4-nitrobenzylphosphonate

生成物 1

HCID 67194189tert-Butyl 4-(2-chloro-5-fluoro-4-nitrobenzylidene)piperidine-1-carboxylate収率 28.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diethyl 2-chloro-5-fluoro-4-nitrobenzylphosphonate (4.06 g, 12.47 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (2.48 g, 12.47 mmol) were stirred in tetrahydrofuran (47.9 ml) and cooled in an ice bath. Sodium hydride (0.65 g, 16.21 mmol) was added and the reaction taken off the ice bath and stirred for 3.5 hours at room temperature. The reaction was quenched with water and extracted with dichloromethane, dried (magnesium sulphate), filtered and evaporated under reduced pressure. The crude material was purified by silica chromatography using a dichloromethane solvent system. The oil obtained was triturated with heptane and filtered to give the title compound as a yellow solid (1.32 g). 1H NMR (CDCl3, 400 MHz): δ 8.12 (d, 1H), 7.13 (d, 1H), 6.33 (s, 1H), 3.55 (t, 2H), 3.44 (t, 2H), 2.41 (t, 2H), 2.34 (t, 2H), 1.48 (s, 9H)

後処理

  1. temperaturecooled in an ice bath
  2. customThe reaction was quenched with water
  3. extractionextracted with dichloromethane
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude material was purified by silica chromatography
  8. customThe oil obtained
  9. customwas triturated with heptane
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-6317c51e91b34c5a8beb84b4aad61965
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09108939B2

反応ノート

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