ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Ammonium Chloride → 1,1-Dimethylethyl 4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinecarboxylate

HRID 1363001
ノート
印刷プレビュー

反応式

HRID 1363001 の反応式
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13](F)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([OH:29])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].CC(C)([O-])C.[Na+].[Cl-].[NH4+]>CN1C(=O)CCC1>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:29][CH:26]3[CH2:25][CH2:24][N:23]([C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])[CH2:28][CH2:27]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 23676156Sodium t-butoxideHCID 579260496-Butyl-8-fluoroquinoline2 回

生成物 1

HCID 579260451,1-Dimethylethyl 4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinecarboxylate

試薬・触媒・溶媒 1

HCID 13387
N-methyl-2-pyrrolidone
溶媒
2 回

実験手順

A solution of 6-butyl-8-fluoroquinoline (for example, as prepared for Intermediate 2) (14.4 g, 70.9 mmol) in NMP (20 ml) was added to a mixture of tert-butyl-4-hydroxy-1-piperidinecarboxylate (commercially available, for example, from Aldrich) (21.6 g, 108 mmol) and sodium tert-butoxide (10.4 g, 108 mmol) in NMP (75 ml), and the resulting mixture was stirred at 140° C. for approximately 90 min and then allowed to cool overnight. The reaction mixture was treated with ammonium chloride solution and extracted with EtOAc (×2). The combined organic extracts were washed with water, dried (MgSO4), filtered and evaporated to dryness. The residue was purified by flash chromatography eluting with DCM-EtOAc (1:0 to 1:1) and then twice by Flashmaster chromatography eluting with DCM-EtOAc (1:0 to 3:1) over 40 min to give the title compound (22 g). LCMS RT=3.49 min, ES+ve m/z 385 [M+H]+

後処理

  1. temperatureto cool overnight
  2. extractionextracted with EtOAc (×2)
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography
  8. washeluting with DCM-EtOAc (1:0 to 1:1)
  9. washtwice by Flashmaster chromatography eluting with DCM-EtOAc (1:0 to 3:1) over 40 min

出典と根拠

ORDレコード
ord-1fc7f3c054c74bffb881bbe71d2c184f
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07884114B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート