Ammonia → 4-(2-Methyl-pentyl)-pyrrolidin-2-one

HRID 479029ノート

反応式

HRID 479029 の反応式
N.C([N:9]1[CH2:13][CH:12]([CH2:14][CH:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH2:11][C:10]1=[O:20])C1C=CC=CC=1.[Na]>C1COCC1>[CH3:19][CH:15]([CH2:16][CH2:17][CH3:18])[CH2:14][CH:12]1[CH2:13][NH:9][C:10](=[O:20])[CH2:11]1

参加物

5

反応物 3

HCID 222AmmoniaHCID 5360545SodiumHCID 218882331-Benzyl-4-(2-methyl-pentyl)-pyrrolidin-2-one

生成物 1

HCID 218881744-(2-Methyl-pentyl)-pyrrolidin-2-one収率 92.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A 250 mL 3-neck flask equipped with a dry ice condenser was chilled to −78° C. Ammonia (80 mL) was condensed into the flask and 1-benzyl-4-(2-methyl-pentyl)-pyrrolidin-2-one 76 (1.67 g, 0.006 mol) in 15 mL THF was added. Freshly cut sodium beads were added until a deep blue color persisted. The cooling bath was removed and the reaction stirred at reflux (−33° C.) for 1 hour. The reaction was quenched with ammonium chloride and the excess ammonia was allowed to evaporate. The resulting residue was diluted with water, extracted with dichloromethane, and dried over magnesium sulfate. Evaporation of the solvent followed by chromatography on silica eluting with 1:1 acetone/hexane gave 0.94 g, 86% of the 4-(2-Methyl-pentyl)-pyrrolidin-2-one 77. 1H NMR (CDCl3) δ6.25 (br, 1H), 3.44 (m, 1H), 2.95 (m, 1H), 2.54 (m, 1H), 2.40 (m, 1H), 1.98 (m, 1H), 1.30 (m, 6H), 0.80 (m, 6H). MS, m/z (relative intensity): 212 [M+2H+CH3CN, 100%], 171 [M+2H, 72%], 170 [M+1H, 65%].

後処理

  1. customA 250 mL 3-neck flask equipped with a dry ice condenser
  2. additionwas added
  3. customThe cooling bath was removed
  4. temperatureat reflux (−33° C.) for 1 hour
  5. customThe reaction was quenched with ammonium chloride
  6. customto evaporate
  7. additionThe resulting residue was diluted with water
  8. extractionextracted with dichloromethane
  9. dry with materialdried over magnesium sulfate
  10. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-32acf88633b2448ea5bce38b86f94078
出典データセット
uspto-grants-2003_11
特許番号
US06642398B2

反応ノート

読み込み中…