Ethylamine → N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide

HRID 364032

反応式

HRID 364032 の反応式
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([C:14]([O:16]C)=O)[CH2:3]1.[CH2:18]([NH2:20])[CH3:19]>CO>[CH2:18]([NH:20][C:14]([CH:4]1[CH2:3][C:2](=[O:1])[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5]1)=[O:16])[CH3:19]

参加物

4

反応物 2

HCID 6341EthylamineHCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate

生成物 1

HCID 13491793N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide収率 49.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 200 g (0.86 mole) of methyl 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylate [J. Org. Chem., 26, 1519 (1961)], 1000 ml methanol and 200 g (4.4 mole) of ethylamine was heated at 100° C. in a pressure reactor for 17.2 hours. The reaction mixture was cooled and the excess ethylamine and methanol were removed under reduced pressure. The residue was taken up in dichloromethane and washed with 3×150 ml 1N sodium hydroxide. The organic layer was dried over magnesium sulfate and the solvent removed at reduced pressure to give 104.6 g of N-ethyl-5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxamide as a white solid, mp 97°-99° C.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customthe excess ethylamine and methanol were removed under reduced pressure
  3. washwashed with 3×150 ml 1N sodium hydroxide
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent removed at reduced pressure

出典と根拠

ORDレコード
ord-3f7bae9d6f1e42a2a0272f57ddd383b6
出典データセット
uspto-grants-1986_08
特許番号
US04604401

関連ノート

読み込み中…