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

Tetrahydrofuran → HCID 66649866、化合物

HRID 419731
ノート
印刷プレビュー

反応式

HRID 419731 の反応式
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=2)[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.O1CCCC1.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][C:44](=[O:47])[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][C:44]([OH:47])([C:11]2[N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:20])[CH3:21])[CH:13]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=3)[N:10]=2)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]
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

6

反応物 4

HCID 8028TetrahydrofuranHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 121144924-(3-Trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 66649866HCID 66649866、化合物収率 79.29%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
-78 °C

実験手順

To a 100 mL round bottom flask (fitted with cooling bath, stir bar and nitrogen blanket) add 4-(3-Trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (0.995 g; 1.00 equiv; 2.91 mmoles; 995.00 mg), n-Butyl Lithium (2.8 mL; 1.54 equiv; 4.48 mmoles; 2.80 mL; 1.90 g), and Tetrahydrofuran (30 mL; 368.66 mmoles; 30.00 mL; 26.58 g) and cool the mixture to −78° C. with stirring on and hold for 30 min. Add N-T-Butoxycarbonyl-4-piperidone (0.706 g; 1.22 equiv; 3.54 mmoles; 706.00 mg) and allow the reaction to warm to room temperature. Dilute the reaction with CH2Cl2, wash with water, dry over Na2SO4, filter, and concentrate to dryness. Purify the crude mixture by flash chromatography on silica eluting with ethyl acetate/hexane from 10-50% EtOAc. Combine the appropriate fractions and concentrate to give 4-Hydroxy-4-[4-(3-trifluoromethyl-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]piperidine-1-carboxylic acid tert-butyl ester (1.248 g; 0.79 equiv; 2.30 mmoles; 1.25 g; 79.29% yield).

後処理

  1. customTo a 100 mL round bottom flask (fitted with cooling bath, stir bar and nitrogen blanket)
  2. customthe reaction
  3. temperatureto warm to room temperature
  4. additionDilute
  5. washwash with water
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate to dryness
  9. customPurify the crude mixture by flash chromatography on silica eluting with ethyl acetate/hexane from 10-50% EtOAc
  10. concentrationconcentrate

出典と根拠

ORDレコード
ord-254020ad9a734b898e8fdf845572dbdf
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093383B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート