Hydrochloric Acid → 1-(4-Methoxybenzyl)-4-methylimidazolidin-2-one

HRID 2411176ノート

反応式

HRID 2411176 の反応式
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][N:10]2[C:14](=O)[CH:13]([CH3:16])[NH:12][C:11]2=[O:17])=[CH:7][CH:6]=1.CO.Cl>O1CCCC1>[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH3:16])[NH:12][C:11]2=[O:17])=[CH:7][CH:6]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 683283563-(4-Methoxybenzyl)-5-methylimidazolidine-2,4-dione

生成物 1

HCID 712520041-(4-Methoxybenzyl)-4-methylimidazolidin-2-one収率 61.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under a nitrogen stream, sodium borohydride (0.65 g) was suspended in tetrahydrofuran (25 mL), boron trifluoride diethyl ether complex (2.63 mL) was added dropwise under ice-cooling, and the mixture was stirred at the same temperature for 15 min. Then, a solution of 3-(4-methoxybenzyl)-5-methylimidazolidine-2,4-dione (2.00 g) described in Preparation Example 51 in tetrahydrofuran (25 ml) was added under ice-cooling, and the mixture was stirred at the same temperature for 30 min and at room temperature overnight. To the reaction mixture were added dropwise methanol and 0.5N hydrochloric acid, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated from the reaction mixture, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.16 g).

後処理

  1. additionboron trifluoride diethyl ether complex (2.63 mL) was added dropwise under ice-
  2. temperaturecooling
  3. additionwas added under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred at the same temperature for 30 min and at room temperature overnight
  6. stirringthe mixture was stirred at room temperature for 1 hr
  7. customThe solvent was evaporated from the reaction mixture, water
  8. additionwas added
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with 1N hydrochloric acid, water and saturated brine
  11. customthe solvent was evaporated
  12. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-58b2a45933304219a31dc525455fd0b6
出典データセット
uspto-grants-2014_08
特許番号
US08816079B2

反応ノート

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