Ammonium Chloride → HCID 178461575、化合物

HRID 1913549ノート

反応式

HRID 1913549 の反応式
[CH3:1][C@H:2]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[C:5](=[O:18])[CH2:4][CH2:3]1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([N:36]2[CH:40]=[C:39]([CH:41]=O)[N:38]=[CH:37]2)[CH2:32][CH2:31]1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][C@H:2]1[CH2:7][NH:6][C:5](=[O:18])/[C:4](=[CH:41]/[C:39]2[N:38]=[CH:37][N:36]([C@H:33]3[CH2:34][CH2:35][C@H:30]([CH3:29])[CH2:31][CH2:32]3)[CH:40]=2)/[CH2:3]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 22872605Benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylateHCID 178461291HCID 178461291、化合物

生成物 1

HCID 178461575HCID 178461575、化合物収率 55.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Benzyl (5R)-5-methyl-2-oxopiperidine-1-carboxylate (Org. Lett, 2009, Vol. 11, p. 5410) (772 mg) was dissolved in tetrahydrofuran (15 mL). To the solution, lithium hexamethyldisilazide (LHMDS, 1 N tetrahydrofuran solution, 3.12 mL) was added dropwise at −78° C., and the mixture was stirred for 1 hour. Subsequently, a solution of 1-(trans-4-methylcyclohexyl)-1H-imidazole-4-carbaldehyde (600 mg) in tetrahydrofuran (5 mL) was added dropwise thereto at −78° C., and the mixture was stirred at 0° C. for 3 hours. To the reaction solution, aqueous ammonium chloride was added, and organic matter was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate-ethyl acetate/methanol=92/8) to obtain the title compound (500 mg).

後処理

  1. stirringat −78° C., and the mixture was stirred at 0° C. for 3 hours
  2. extractionorganic matter was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a crude product
  7. customThis crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate-ethyl acetate/methanol=92/8)

出典と根拠

ORDレコード
ord-a4395665ce1a44eeb3e765375bcf5391
出典データセット
uspto-grants-2013_12
特許番号
US08609710B2

反応ノート

読み込み中…