Ammonium Chloride → (2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(4,4,4-trifluoro-3-phenyl-butyl)-2,5-dihydro-pyrazine

HRID 1026109ノート

反応式

HRID 1026109 の反応式
[CH3:1][O:2][C:3]1[C@@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[CH2:7][N:8]=1.C([Li])(C)(C)C.I[CH2:20][CH2:21][CH:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23]([F:26])([F:25])[F:24].[Cl-].[NH4+]>O1CCCC1>[CH:11]([C@@H:4]1[C:3]([O:2][CH3:1])=[N:8][C@@H:7]([CH2:20][CH2:21][CH:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23]([F:25])([F:26])[F:24])[C:6]([O:9][CH3:10])=[N:5]1)([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 736066(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazineHCID 67178112(3-Iodo-1-trifluoromethylpropyl)-benzeneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 67177689(2R,5S)-2-Isopropyl-3,6-dimethoxy-5-(4,4,4-trifluoro-3-phenyl-butyl)-2,5-dihydro-pyrazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (R)-(−)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (1.1 g) in tetrahydrofuran (25 ml) was cooled to −70° C., then tert.butyllithium (1.7 M in pentane, 3.88 ml) was added and the mixture was stirred for 1 hour. A solution of (3-iodo-1-trifluoromethylpropyl)-benzene (1.98 g) in tetrahydrofuran (7 ml) was added slowly and the mixture was stirred overnight at −70° C. At room temperature saturated ammonium chloride solution was added and the mixture was extracted three times with ether. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1 to yield a yellow liquid, (1.86 g, 83%).

後処理

  1. stirringthe mixture was stirred overnight at −70° C
  2. extractionthe mixture was extracted three times with ether
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1
  7. customto yield a yellow liquid, (1.86 g, 83%)

出典と根拠

ORDレコード
ord-959df4cef5a74adc8a52051a4f39fecf
出典データセット
uspto-grants-2014_05
特許番号
US08729113B2

反応ノート

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