Hydrochloric Acid → 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane

HRID 2399854ノート

反応式

HRID 2399854 の反応式
[CH2:1]([C@H:8]([N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])[C@@H:9](OS(C)(=O)=O)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl>O1CCCC1.ClCCl.O>[C:2]1([CH2:1][C@@H:8]([C@H:9]2[CH2:10][O:11]2)[N:17]2[C:18](=[O:27])[C:19]3=[CH:26][CH:25]=[CH:24][CH:23]=[C:20]3[C:21]2=[O:22])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2 回HCID 9977634N-[1(S)-benzyl-3-hydroxy-2(R)-(methylsulphonyloxy)propyl]phthalimide

生成物 1

HCID 102663882(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane収率 41.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

2.16 g of N-[1(S)-benzyl-3-hydroxy-2(R)-(methylsulphonyloxy)propyl]phthalimide were added to a stirred suspension of 200 mg of sodium hydride (80% dispersion in mineral oil) in 50 ml of dry tetrahydrofuran and the mixture was stirred at 20° C. for 2 hours. A further 100 mg of sodium hydride were added and the stirring was continued for 3.5 hours. The mixture was diluted with dichloromethane and water and the pH of the aqueous layer was adjusted to 7 by adding 2M hydrochloric acid. The organic layer was separated, washed with saturated sodium chloride solution and evaporated. The residue was chromatographed on silica gel using ethyl acetate/n-hexane (1:2) for the elution to give 0.67 g of 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane as a white solid, MS: m/e 294 [M+H]+.

後処理

  1. waitthe stirring was continued for 3.5 hours
  2. customThe organic layer was separated
  3. washwashed with saturated sodium chloride solution
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

出典と根拠

ORDレコード
ord-2429a184f5694cad8dab97422d9b6653
出典データセット
uspto-grants-1995_09
特許番号
US05451678

反応ノート

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