1,3-Dichloro-5,5-dimethylhydantoin → 1-(6-Chloro-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine

HRID 2416607

反応式

HRID 2416607 の反応式
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[Cl:27]N1C(C)(C)C(=O)N(Cl)C1=O.[OH-].[Na+]>O1CCCC1.CCCCC>[Cl:27][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 14798Sodium HydroxideHCID 22478562Tert-butyl 4-(6-bromopyridin-3-yl)-1,4-diazepane-1-carboxylateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 224784871-(6-Chloro-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A stirred solution of 1-(6-Bromo-3-pyridyl)-4-tert-butoxycarbonyl homopiperazine (3.6 g, 10 mmol) in tetrahydrofuran (200 ml) was cooled to −78° C. Tert-butyllithium (14.7 ml, 1.5 M) in pentane was added during 10 min, followed by stirring for 5 min at −78° C. 1,3-Dichloro-5,5-dimethylhydantoin (1.97 g, 10 mmol) was added in small portions. The mixture was stirred for 0.5 min. Aqueous sodium hydroxide was added (100 ml, 4 M), and the reaction was allowed reach room temperature. The mixture was extracted twice with diethyl ether (100 ml) Chromatography on silica gel with a mixture of petroleum:ethyl acetate (1:1) gave the title compound as free base. Yield 1.7 g, 55%.

後処理

  1. stirringThe mixture was stirred for 0.5 min
  2. customreach room temperature
  3. extractionThe mixture was extracted twice with diethyl ether (100 ml) Chromatography on silica gel with a mixture of petroleum:ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-d75e475319114f4989e4078b8186e13a
出典データセット
uspto-grants-2004_11
特許番号
US06825189B1

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