Imidazole → (R)-t-Butyl 2-((t-butyldimethylsilyloxy)methyl)piperazine-1-carboxylate

HRID 876012

反応式

HRID 876012 の反応式
[OH:1][CH2:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Si:20]([O:1][CH2:2][C@H:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

参加物

6

反応物 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 24820219(R)-2-Hydroxymethyl-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 58299667(R)-t-Butyl 2-((t-butyldimethylsilyloxy)methyl)piperazine-1-carboxylate収率 60.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(R)-t-Butyl 2-(hydroxymethyl)piperazine-1-carboxylate (1.15 g, 5.32 mmol), t-butylchlorodimethylsilane (0.882 g, 5.85 mmol), and imidazole (0.796 g, 11.7 mmol) were stirred in dichloromethane (3 mL) for three days. The solution was added to aqueous K2CO3 (30 mL) and extracted with dichloromethane (3×30 mL). The combined organics were dried (MgSO4) and evaporated to give a yellow oil. Silica gel chromatography (gradient elution hexanes/0-50% ethyl acetate) afforded compound 308 as a colorless oil (1.06 g, 60%).

後処理

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil
  5. washSilica gel chromatography (gradient elution hexanes/0-50% ethyl acetate)

出典と根拠

ORDレコード
ord-7282317f085f4061830c5b73a88005a5
出典データセット
uspto-grants-2015_03
特許番号
US08980903B2

関連ノート

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