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

HRID 1173740ノート

反応式

HRID 1173740 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-03d6ef1815f1471f84d70f0b45f264fc
出典データセット
uspto-grants-2010_11
特許番号
US07834051B2

反応ノート

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