Sodium bis(trimethylsilyl)amide → HCID 68743645、化合物

HRID 238656

反応式

HRID 238656 の反応式
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:11]([C:13]1[N:14]=[C:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[S:16][CH:17]=1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.O>[CH:11]([C:13]1[N:14]=[C:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[S:16][CH:17]=1)=[CH2:1]

参加物

6

反応物 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 7172298tert-Butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate

生成物 1

HCID 68743645HCID 68743645、化合物収率 95.2%

試薬・触媒・溶媒 3

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a cold (−50° C.) suspension of methyltriphenylphosphonium bromide (1.2 g, 3.3 mmol) in tetrahydrofuran (5 mL) was added a solution of sodium bis(trimethylsilyl)-amide (3.4 mL, 3.4 mmol), and the resulting mixture was stirred for 1 h at room temperature. The resulting cloudy yellow solution was re-cooled to −30° C., and 1,1-dimethylethyl 4-(4-formyl-2-thiazolyl)-1-piperidinecarboxylate (0.5 g, 1.68 mmol) was added. The resulting slightly yellow solution was stirred at room temperature for 3 h, then diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and purified by column chromatography on silica gel using 15-30% ethyl acetate in hexanes as eluant to give 471 mg of the title compound as a colorless oil.

後処理

  1. temperatureThe resulting cloudy yellow solution was re-cooled to −30° C.
  2. stirringThe resulting slightly yellow solution was stirred at room temperature for 3 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. custompurified by column chromatography on silica gel using 15-30% ethyl acetate in hexanes as eluant

出典と根拠

ORDレコード
ord-7380437b47cf487f823e37a08c17453c
出典データセット
uspto-grants-2014_02
特許番号
US08642634B2

関連ノート

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