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

Imidazole → pyrrolizine-3,5(2H,6H)-dione

HRID 653390
ノート
印刷プレビュー

反応式

HRID 653390 の反応式
[O:1]=[C:2]1[NH:6][CH:5]([CH2:7][CH:8](O)[C:9]([OH:11])=O)[CH2:4][CH2:3]1.[Si](Cl)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.N1C=CN=C1>CN(C)C=O.O>[CH2:4]1[C:5]2[N:6]([C:9](=[O:11])[CH2:8][CH:7]=2)[C:2](=[O:1])[CH2:3]1
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 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 201946205-Oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid

生成物 1

HCID 11819136pyrrolizine-3,5(2H,6H)-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A solution of 5-oxo-alpha-hydroxy-2-pyrrolidinepropanoic acid (1.73 g), t-butyl-diphenylsilyl chloride (11 g), and imidazole (5.4 g) is allowed to stir in dimethylformamide (50 ml) for six hours at room temperature. The solution is diluted with water (100 mL) and extracted with diethyl ether (4×100 mL). The combined extracts are concentrated and the oil is dissolved in methanol (50 mL) and a 10% aqueous solution of potassium carbonate (50 mL) is added and the solution is stirred 18 hours. The solution is concentrated and washed with saturated brine (50 mL) and extracted with diethyl ether (4×75 mL). The combined extracts are dried and concentrated to an oil. The oil is dissolved in acetic anhydride (50 mL) and the solution is heated at 90° C. for two hours. The solution is filtered hot, concentrated, and the residue purified by chromatography on SiO2 (elution with chloroform:methanol; 99:1) to yield cis- and trans-2-t-butyl-diphenyllsilyloxy-dihydro-1H)-pyrrolizine-3,5(2H,6H )-dione as a white solid with mp 155°-156° C. NMR (CDCl3) and 7.60 (m, 10H), 4.66 (m, 1/2H), 4.40 (dd, 1H), 3.86 (m, 1/2H), 2.77-1.55 (m, 6H), 1.08 (s, 9H). IR (KBr) 3074, 2933, 1858, 1791, 1705, 1591, 1474, 1430, 1380, 1313, 1279.

後処理

  1. extractionextracted with diethyl ether (4×100 mL)
  2. concentrationThe combined extracts are concentrated
  3. dissolutionthe oil is dissolved in methanol (50 mL)
  4. additiona 10% aqueous solution of potassium carbonate (50 mL) is added
  5. concentrationThe solution is concentrated
  6. washwashed with saturated brine (50 mL)
  7. extractionextracted with diethyl ether (4×75 mL)
  8. customThe combined extracts are dried
  9. concentrationconcentrated to an oil
  10. dissolutionThe oil is dissolved in acetic anhydride (50 mL)
  11. filtrationThe solution is filtered hot
  12. concentrationconcentrated
  13. customthe residue purified by chromatography on SiO2 (elution with chloroform:methanol; 99:1)

出典と根拠

ORDレコード
ord-92682912ef6b4aff8c1d54fba4f44de5
出典データセット
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04677098

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