Potassium Carbonate → tert-butyl 4-(((2,5-dimethyl-1H-imidazol-4-yl)methyl)amino)-1-piperidinecarboxylate

HRID 1162331ノート

反応式

HRID 1162331 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]1[NH:17][C:18]([CH3:23])=[C:19]([CH:21]=O)[N:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.C(O)(=O)C>[CH3:15][C:16]1[NH:17][C:18]([CH3:23])=[C:19]([CH2:21][NH:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[N:20]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 132064322,5-Dimethyl-1H-imidazole-4-carbaldehyde

生成物 1

HCID 23138170tert-butyl 4-(((2,5-dimethyl-1H-imidazol-4-yl)methyl)amino)-1-piperidinecarboxylate収率 108.2%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

実験手順

N-(tert-butoxycarbonyl-4-piperidinyl)amine (4.8 g), 2,5-dimethylimidazole-4-carbaldehyde (3.0 g) and acetic acid (1.7 ml) were dissolved in 1,2-dichloroethane (50 ml), under ice-cooling, sodium triacetoxyborohydride (7.7 g) was added thereto, and mixed at room temperature for 15 hours. The reaction solution was poured into an aqueous potassium carbonate solution, and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and then the residue was purified with silica gel column to obtain a pale yellow oily title compound (8.0 g, quantitative).

後処理

  1. temperaturecooling
  2. additionmixed at room temperature for 15 hours
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified with silica gel column

出典と根拠

ORDレコード
ord-129d51e43502499fab431054ed92145d
出典データセット
uspto-grants-2010_10
特許番号
US07820673B2

反応ノート

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