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Ammonium Chloride → (2S,5R)-2-[2-(2-Chloro-phenyl)-ethyl]-5-isopropyl-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine

HRID 1911550
ノート
印刷プレビュー

反応式

HRID 1911550 の反応式
[CH3:1][O:2][C:3]1[C@@H:4]([CH:12]([CH3:14])[CH3:13])[N:5]=[C:6]([O:10][CH3:11])[CH:7]([CH3:9])[N:8]=1.C([Li])(C)(C)C.Br[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29].[Cl-].[NH4+]>O1CCCC1>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][C@@:7]1([CH3:9])[C:6]([O:10][CH3:11])=[N:5][C@H:4]([CH:12]([CH3:14])[CH3:13])[C:3]([O:2][CH3:1])=[N:8]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 27569631-(2-Bromoethyl)-2-chlorobenzeneHCID 11481040(R)-(-)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-methylpyrazineHCID 178418306HCID 178418306、化合物

生成物 1

HCID 68716087(2S,5R)-2-[2-(2-Chloro-phenyl)-ethyl]-5-isopropyl-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

A solution of (R)-(−)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-methylpyrazine (1.0 g, 5.0 mmol) in tetrahydrofuran (23 ml) was cooled to −70° C., then tert.butyllithium (1.7 M in pentane, 3.26 ml, 5.55 mmol) was added and the mixture was stirred for 1 hour. A solution of 1-(2-bromo-ethyl)-2-chlorobenzene (1.44 g, 6.56 mmol) in tetrahydrofuran (10 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=1:1 to yield an orange solid, (1.22 g, 72%); MS (ISP): 337.1; 339.1 ((M+H)+.).

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=1:1
  7. customto yield an orange solid, (1.22 g, 72%)

出典と根拠

ORDレコード
ord-1f8d0e6aa34744169bd4ce39625a625d
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08604061B2

反応ノート

読み込み中…

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