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

HRID 376002노트

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HRID 376002 반응식
[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

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2회HCID 9977634N-[1(S)-benzyl-3-hydroxy-2(R)-(methylsulphonyloxy)propyl]phthalimide

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-f0bb9285bfbb436e9ec7fbdcf4811f9d
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488115

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