Ammonium Chloride → HCID 22032377、化合物

HRID 1792497ノート

反応式

HRID 1792497 の反応式
Br[C:2]1[S:3][C:4]([S:7][CH3:8])=[CH:5][CH:6]=1.C([Li])CCC.[CH:14]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15].[Cl-].[NH4+]>O1CCCC1.CCCCCC.O>[OH:15][CH:14]([C:2]1[S:3][C:4]([S:7][CH3:8])=[CH:5][CH:6]=1)[CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 220320322-broMo-5-(Methylthio)thiopheneHCID 178418339Butyllithium

生成物 1

HCID 22032377HCID 22032377、化合物収率 73%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

1.2 g of 2-bromo-5-(methylsulfanyl)thiophen (compound in Production Example 45) was dissolved in 20 mL anhydrous tetrahydrofuran, and 3.72 mL solution of 1.59 M n-butyl lithium in hexane was added dropwise there to at −70° C. After the mixture was stirred for 1 hour, 6 ml solution of 1.2 g t-butyl 4-formyl-piperidine-1-carboxylate in anhydrous tetrahydrofuran was added dropwise thereto and stirred at −70° C. for 2 hours. The temperature of the reaction solution was gradually increased to 0° C., water and an ammonium chloride solution were added thereto, and the reaction solution was extracted with ethyl acetate. The extract was dried over magnesium sulfate and purified by silica gel column chromatography (ethyl acetate/hexane), to give 1.41 g of the title compound as pale pink crystals.

後処理

  1. stirringstirred at −70° C. for 2 hours
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. custompurified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-d25aea702e9447dabf441251e5cc1cd6
出典データセット
uspto-grants-2006_07
特許番号
US07074801B1

反応ノート

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