Sodium hydride → HCID 67194178、化合物

HRID 515363ノート

反応式

HRID 515363 の反応式
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH2:9]P(=O)(OCC)OCC)([O-:5])=[O:4].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>O1CCCC1>[N+:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH:9]=[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)([O-:5])=[O:4]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 13675396Diethyl 3-Nitrobenzylphosphonate

生成物 1

HCID 67194178HCID 67194178、化合物収率 85.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of sodium hydride (10.98 mmol, 0.439 g) in tetrahydrofuran (40 mL) was added to a stirred solution of diethyl 3-nitrobenzylphosphonate (7.32 mmol, 2 g) in tetrahydrofuran (40 mL) at 0° C. and the reaction stirred for 30 minutes. tert-Butyl 4-oxopiperidine-1-carboxylate (7.32 mmol, 1.459 g) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue partitioned between dichloromethane and water. The organic layer was separated, dried and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: 0-2% methanol in dichloromethane) to afford the intermediate tert-butyl 4-(3-nitrobenzylidene)-piperidine-1-carboxylate (2 g).

後処理

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica column chromatography (eluent: 0-2% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-a14bae850ae94b83b168e5dc37ffa3db
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

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