Acetic Acid → 2-chloro-4-[(2S,3S)-2-(cyclopropylmethyl)-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile

HRID 1173740노트

반응식

HRID 1173740 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C:14](=[O:15])[CH:13]=[C:12]([OH:16])[CH:11]2[CH2:17][CH:18]2[CH2:20][CH2:19]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O)(=O)C.[BH4-].[Na+].O>C(#N)C>[Cl:1][C:2]1[CH:9]=[C:8]([N:10]2[C:14](=[O:15])[CH2:13][C@H:12]([OH:16])[C@@H:11]2[CH2:17][CH:18]2[CH2:20][CH2:19]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 595569612-chloro-4-[2-(cyclopropylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]benzonitrile

생성물 1

HCID 595570292-chloro-4-[(2S,3S)-2-(cyclopropylmethyl)-3-hydroxy-5-oxopyrrolidin-1-yl]benzonitrile수율 77%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of 2-chloro-4-[2-(cyclopropylmethyl)-3-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl]benzonitrile (400 mg) and acetic acid (0.87 mL) in acetonitrile (10 mL) was added sodium borohydride (131 mg) at 0° C. in small portions. The mixture was warmed to room temperature and stirred for 1 hr. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1→ethyl acetate), and recrystallized from tetrahydrofuran-hexane to give the title compound as colorless crystals (yield: 310 mg, 77%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1→ethyl acetate)
  6. customrecrystallized from tetrahydrofuran-hexane

출처 및 근거

ORD 기록
ord-03d6ef1815f1471f84d70f0b45f264fc
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

반응 노트

불러오는 중…