tert-Butyl hydroperoxide → 4-Oxiranecarbonyl piperazine-1-carboxylic acid tert butyl ester

HRID 1694879ノート

反応式

HRID 1694879 の反応式
C([O:5]O)(C)(C)C.C([Li])CCC.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25](=[O:28])[CH:26]=[CH2:27])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].S([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(OCC)C>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][N:22]([C:25]([CH:26]2[CH2:27][O:5]2)=[O:28])[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

参加物

7

反応物 4

HCID 6410tert-Butyl hydroperoxideHCID 24437Sodium SulfiteHCID 58593060tert-Butyl 4-acryloylpiperazine-1-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 867011264-Oxiranecarbonyl piperazine-1-carboxylic acid tert butyl ester収率 19.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of anhydrous t-butyl hydroperoxide (5.5M in nonane, 2.07 ml, 11.38 mmol, 1.5 eq) was added to anhydrous THF (50 mL), at −78° C. under argon. To the resulting solution at −78° C. was added butyl lithium (2.3M in n-hexane, 3.36 ml, 8.4 mmol, 1.1 eq) was added and the solution is stirred for a further 5 min at this temperature. A solution of the 4-Acryloyl-piperazine-1-carboxylic acid tert butyl ester (1.96 g, 7.64 mmol, 1 eq) in anhydrous THF (20 ml) was then added dropwise at −78° C. The resulting mixture was then allowed to warm slowly to room temperature and stirred for a further 16 hr. To the mixture was then added sodium sulfite (1.5 g, 12 mmol, 1.55 eq) and this was then stirred for 15 min. The mixture was then diluted with diethylether (50 ml), filtered through celite and the filtrate evaporated. The residue was purified by chromatography (ethyl acetate/n-hexane 4/1) to give the product (0.39 g, 19%) as a white solid.

後処理

  1. additionwas added
  2. stirringstirred for a further 16 hr
  3. filtrationfiltered through celite
  4. customthe filtrate evaporated
  5. customThe residue was purified by chromatography (ethyl acetate/n-hexane 4/1)

出典と根拠

ORDレコード
ord-ef6704291b3f4c789480f290dcf64860
出典データセット
uspto-grants-2012_04
特許番号
US08158797B2

反応ノート

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