Benzyl Bromide → Methyl 1-benzyl-5-oxo-2-pyrrolidinecarboxylate

HRID 253167

反応式

HRID 253167 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:11][CH2:10][C:9](=[O:12])[NH:8]1)=[O:6].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1C=CC=CC=1>[CH3:3][O:4][C:5]([CH:7]1[CH2:11][CH2:10][C:9](=[O:12])[N:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:6]

参加物

5

反応物 3

HCID 7498Benzyl Bromide2 回HCID 24758Sodium hydrideHCID 500249Methyl 5-oxo-DL-prolinate

生成物 1

HCID 11096495Methyl 1-benzyl-5-oxo-2-pyrrolidinecarboxylate収率 52.6%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

反応条件

温度
45 °C

実験手順

To a slurry of NaH (22 g of 60% NaH in mineral oil, 0.55 mol) in 400 mL benzene was added the product of Example 1A (0.387 mol) in 100 mL benzene dropwise via addition funnel. The mixture stirred for 30 minutes after the addition was complete, then was warmed to reflux and allowed to stir for 1.5 h. The reaction was cooled to 45° C. and stirred for 16 h. A portion of benzyl bromide (45 mL, 0.38 mol) was added, the mixture was warmed to reflux and an additional amount of benzyl bromide was added (45 mL, 0.38 mol). This solution stirred for 24 h at reflux, then was cooled to ambient temperature, filtered through Celite® diatomaceous earth and the residue was washed with CH2Cl2. The combined filtrates were concentrated under reduced pressure and excess benzyl bromide was removed via distillation. The distillation residue was purified via column chromatography (SiO2, 75% hexanes-EtOAc) to give 46.6 g of the title compound (0.2 mol, 52% yield). MS (DCl/NH3) m/z 234 (M+H)+.

後処理

  1. additiondropwise via addition funnel
  2. additionafter the addition
  3. temperaturewas warmed
  4. temperatureto reflux
  5. stirringto stir for 1.5 h
  6. stirringstirred for 16 h
  7. temperaturethe mixture was warmed
  8. temperatureto reflux
  9. stirringThis solution stirred for 24 h
  10. temperatureat reflux
  11. temperaturewas cooled to ambient temperature
  12. filtrationfiltered through Celite® diatomaceous earth
  13. washthe residue was washed with CH2Cl2
  14. concentrationThe combined filtrates were concentrated under reduced pressure and excess benzyl bromide
  15. customwas removed via distillation
  16. distillationThe distillation residue was purified via column chromatography (SiO2, 75% hexanes-EtOAc)

出典と根拠

ORDレコード
ord-ed3e4bf0299941629b9e017951b82d9c
出典データセット
uspto-grants-2011_01
特許番号
US07872010B2

関連ノート

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