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Imidazole → Tert-butyl 4-(1H-imidazol-1-YL)piperidine-1-carboxylate

HRID 392501
ノート
印刷プレビュー

反応式

HRID 392501 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件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 795ImidazoleHCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

生成物 1

HCID 22662911Tert-butyl 4-(1H-imidazol-1-YL)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of the title compound from Step B (4.0 g, 14.32 mmoles) in DMF (120 mL) was added to a stirred solution of NaH (0.52 g, 21.66 mmoles) and imidazole (1.46 g, 21.47 mmoles) in DMF (20 mL) under nitrogen atmosphere. The mixture was stirred at 60° C. for 16 h. DMF was evaporated in vacuo. The resulting crude product was extracted with CH2Cl2 and the extract was successively washed with water and brine, and the CH2Cl2 was evaporated to leave the title residue which was chromatographed on silica gel using 3% (10% cone NH4OH in methanol)-CH2Cl2 as eluant to give the title compound (0.94 g, 26%). FABMS (M+1)=252; δH (CDCl3) 1.4 (s, 9H), 1.6-1.8 (m, 2H), 2.0 (dd, 2H), 2.8 (dt, 2H), 4.05 (m, 1H), 4.2 m, 2H), 6.9 (s, 1H), 7.0 (s, 1H), 7.65 (s, 1H).

後処理

  1. customDMF was evaporated in vacuo
  2. extractionThe resulting crude product was extracted with CH2Cl2
  3. washthe extract was successively washed with water and brine
  4. customthe CH2Cl2 was evaporated

出典と根拠

ORDレコード
ord-bb3160eb51e34cf0ad408352b27c3d74
出典データセット
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06800636B2

反応ノート

読み込み中…

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