Hydrochloric Acid → 1-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate

HRID 341770

反応式

HRID 341770 の反応式
[H-].[Na+].C(O[C:6](=[O:16])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].Cl.CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C>C1COCC1.CCOCC>[CH2:22]([O:21][C:17]([CH:18]1[C:6](=[O:16])[CH2:7][N:8]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:19]1)=[O:20])[CH3:23]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 24758Sodium hydrideHCID 357729Ethyl 2-((tert-butoxycarbonyl)amino)acetate

生成物 1

HCID 108689421-tert-Butyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate収率 71%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a refluxing suspension of 1.58 g (66 mmol) sodium hydride in 100 ml THF was added dropwise a solution of 12.79 g (60 mmol) N-tert-butyloxycarbonyl-glycine ethyl ester and 7.15 g (66 mmol) ethyl acrylate in 100 ml THF. After the addition was complete the mixture was heated to reflux for additional 2 h. The clear solution was cooled to room temperature, poured on 100 ml ether/100 ml water and acidified under vigorous stirring with 1N hydrochloric acid against methyl orange. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic layers were washed with sat. sodium bicarbonate and brine, dried over MgSO4 and evaporated. Short-path distillation of the residue gave 10.92 g (71%) 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert. butylester 3-ethylester as a colorless oil, b.p. 119°-122° C. (0.2 mbar), which solidified on prolonged standing in the freezer.

後処理

  1. additionAfter the addition
  2. temperaturewas heated
  3. temperatureto reflux for additional 2 h
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted three times with ether
  6. washThe combined organic layers were washed with sat. sodium bicarbonate and brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. distillationShort-path distillation of the residue

出典と根拠

ORDレコード
ord-465369b8f60c46f9bab61dbad1988d8b
出典データセット
uspto-grants-1999_01
特許番号
US05856309

関連ノート

読み込み中…