Dimethylformamide → Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylate

HRID 467783ノート

反応式

HRID 467783 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23](Br)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>[Cu]Br.C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.O>[C:12]([O:16][C:17]([N:19]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:20]1[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:24][N:25]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 31268PyrrolidineHCID 86660188Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate

生成物 1

HCID 70098560Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-pyrrolidin-1-yl-pyrazine-2-carboxylate収率 75.5%

試薬・触媒・溶媒 3

HCID 11762Binol触媒HCID 24593copper(I) bromide触媒HCID 962Water溶媒

実験手順

A pre-dried flask was charged with copper(I) bromide (0.35 mg, 2.89 μmol), (R)-(+)-1,1′-bi-2-naphthol (1.66 mg, 5.78 μmol) and cesium carbonate (113 mg, 347 μmol) under argon atmosphere. DMF (0.5 ml), methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (50 mg, 116 μmol) and pyrrolidine (14.3 μl, 174 μmol) were added and the reaction mixture was stirred at r.t. for 1.5 h. The reaction mixture was poured into water (10 ml) and extracted with ethyl acetate. The combined organic layer was washed with brine, dried, evaporated and purified by silica gel chromatography using a heptane/ethyl acetate gradient to yield the product as yellow solid (37 mg, 68%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. customevaporated
  5. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-d8a86a22568446cbb0ceb3e1fa1820b6
出典データセット
uspto-grants-2014_01
特許番号
US08623866B2

反応ノート

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