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

HRID 130521노트

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HRID 130521 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 218881744-(2-Methyl-pentyl)-pyrrolidin-2-one수율 92.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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%].

후처리

  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

출처 및 근거

ORD 기록
ord-2ce8cebfab82474faa86942a9f507cee
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381747B2

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