Hydrochloric Acid → benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylate

HRID 2249677노트

반응식

HRID 2249677 반응식
[CH3:1][CH:2]([CH3:28])[CH2:3][CH:4]=[CH:5][C@@H:6]1[CH2:10][C@@H:9]([O:11]C2CCCCO2)[CH2:8][N:7]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].Cl.C(Cl)(Cl)Cl.O>O1CCCC1>[OH:11][C@H:9]1[CH2:8][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C@H:6]([CH:5]=[CH:4][CH2:3][CH:2]([CH3:28])[CH3:1])[CH2:10]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6212ChloroformHCID 86630053benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-pyrrolidinecarboxylate

생성물 1

HCID 86630054benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylate수율 91.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In 12 ml of tetrahydrofuran is dissolved 0.60 g of benzyl (2S,4R)-2-(4-methyl-1-pentenyl)-4-(tetrahydro-2H-pyran-2-yloxy)-1-pyrrolidinecarboxylate, to which is added 12 ml of 6 mol/L hydrochloric acid. The mixture thus obtained is stirred at ambient temperature for 2 hours. A mixture of chloroform and water is added to the reaction mixture, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=2:1) to obtain 0.43 g of benzyl (2S,4R)-4-hydroxy-2-(4-methyl-1-pentenyl)-1-pyrrolidinecarboxylate as a light yellow oily product.

후처리

  1. customThe mixture thus obtained
  2. additionis added to the reaction mixture
  3. customthe organic layer is separated
  4. customThe organic layer thus obtained
  5. washis washed with water and saturated aqueous solution of sodium chloride successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-10edb66359e64cf08090efcf4751bb29
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314888B1

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