Ammonium Chloride → HCID 70234416、化合物

HRID 850607

反応式

HRID 850607 の反応式
[CH2:1]([NH:8][C@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22]([O:26][C:27](=[O:37])[CH:28]=[CH:29][C:30]1[CH:31]=[N:32][C:33]([NH2:36])=[CH:34][CH:35]=1)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[C:22]([O:26][C:27](=[O:37])[CH2:28][C@@H:29]([C:30]1[CH:31]=[N:32][C:33]([NH2:36])=[CH:34][CH:35]=1)[N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])([CH3:25])([CH3:23])[CH3:24]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 1268086(+)-BenzylphenethylamineHCID 536654623-(6-Amino-pyridin-3-yl)-acrylic acid tert-butyl esterHCID 178418339Butyllithium

生成物 1

HCID 70234416HCID 70234416、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) solution of (R)-(+)-N-benzyl-α-methylbenzylamine (4.0 g, 19 mmol) in 50 mL THF was gradually added n-butyllithium (11.3 mL, 2.5 M, 28.2 mmol) over 5 min. The mixture was stirred for 30 min at 0° C. and cooled to -78° C. A solution of 9-2 (2.0 g, 9.4 mmol) in 20 mL THF was gradually added. After stirring for 40 min at -78° C., it was treated with NH4Cl (sat.) at -78° C., warmed to room temperature and extracted three times with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After solvent evaporation, the residue was purified using silica gel flash chromatography (EtOAc/hexanes, 1:2) to afford the desired product 9-3 as an oil.

後処理

  1. customover 5 min
  2. temperaturecooled to -78° C
  3. stirringAfter stirring for 40 min at -78° C.
  4. temperaturewarmed to room temperature
  5. extractionextracted three times with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. customAfter solvent evaporation
  9. customthe residue was purified

出典と根拠

ORDレコード
ord-a3a1a044c4b7454fab5ee1e58e0d02ce
出典データセット
uspto-grants-2000_01
特許番号
US06017926

関連ノート

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