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

HRID 1167900ノート

反応式

HRID 1167900 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) δ 6.25 (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-1864ee88e0e94e17ba917164c63f006b
出典データセット
uspto-grants-2003_09
特許番号
US06620829B2

反応ノート

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